Real Estate Pros · April 20, 2026 · 15 min listen

Proven Strategies for Real Estate Success: Insights from a Veteran Investor

Show summary

In this insightful interview, Chicago-based real estate investor Lisa Rosenberg shares her journey from a chemist and business owner to a seasoned real estate investor. She discusses evaluating opportunities in Chicago, the importance of proximity, managing properties, and her current projects, offering valuable tips for aspiring investors.

Key takeaways

Lisa bought a Wicker Park property for $80,000 in 1983 when the neighborhood was considered rough, and later sold it for $1.5 million after it gentrified.
She considers the South and West sides of Chicago, including near Garfield Park, to currently have the best opportunity, aided by gentrification spreading from projects like the Obama Library.
Investors can either buy already-renovated properties on Chicago's South Side or take on a full gut renovation if they have the capital, as she did with her own historic renovation.
Proximity to your rental property matters, especially for first-time investors, because it lets you catch tenant or property problems early rather than finding out too late, as happened when she returned from a five-day trip to find a tenant's unit broken into and an appliance destroyed.
She and her husband chose to self-manage tenants rather than hire a property management company, partly out of distrust that some management offers were really attempts to take over the property; she advises people who don't want to deal with tenants directly to find a good management company instead.
Rising rents and cost of living are a growing concern in Chicago, with studio apartments running around $1,500, though still more affordable than New York or California where some landlords ask for six months' deposit.
She is currently exploring two strategies: reaching out to motivated sellers who hold 2-3% mortgages and may need to sell urgently, and land flipping, which she notes requires some capital to get started.

In this episode

About the guest

Lisa Terracina Rosenberg is a Chicago-based real estate investor who grew up around her parents' commercial and residential properties, later taking on rent collection, management, and repairs as they aged. She previously ran Arel Fine Linens, a high-end imported linens brand, handling marketing and PR, and also has a background as a chemist. She has invested in Chicago neighborhoods including Wicker Park since 1983 and is currently exploring deals with sellers who hold low-rate mortgages and land flipping.

Listen to the audio

“I invested in Wicker Park when nobody was investing in Wicker Park, which was 1983. And I bought my property for $80,000 and I sold it for 1.5 million.”
Lisa Terracina Rosenberg

“When you’re on the premises, you see stuff like that. When you’re miles and miles away, you can’t deal with it. And so that’s the advantage that you can nip things in the bud.”
Lisa Terracina Rosenberg

“It's all about the numbers. If the numbers don't work, you shouldn't buy it.”
Lisa Terracina Rosenberg

Chicago real estateproperty managementgentrificationmotivated sellerslow-rate mortgage sellersland flippingtenant managementhistoric renovation

Questions answered in this episode

What areas of Chicago does Lisa Rosenberg think have the best investment opportunity right now?

She points to the South and West sides of Chicago, including near Garfield Park, as areas with opportunity, partly driven by gentrification spreading from projects like the Obama Library. She notes some renovated properties are already available there, or investors with capital can do a full gut renovation.

How important is living near your rental property?

Lisa says proximity is very important, especially for first-time investors, because it lets you catch problems early and deal with tenants directly. She shares a story of a tenant's ex-husband breaking into a unit through a second-floor window while she was out of town for five days, which she only found out about after the fact because she wasn't close by to notice sooner.

What is Lisa's view on property management companies versus self-managing?

She and her husband always managed their own tenants rather than hiring a property manager, partly because people who offered to manage for her seemed more interested in acquiring the property than managing it well. She says if you're the type of person who doesn't want to deal with people directly, a management company is the way to go, but you need to find a good one.

What is Lisa's big early investing win in Chicago?

She bought a property in Wicker Park in 1983 for $80,000 when the neighborhood was considered sketchy (she describes it as having 300 people on the street with her being the only white person, and feral dogs running in packs). She eventually sold that property for $1.5 million after the neighborhood gentrified over time.

What concerns does Lisa have about investing in Illinois/Chicago long term?

She's concerned about the state of Illinois's tax situation given its pension and school funding problems, and worries about where that leaves property taxes going forward. She also cites rising crime and rapidly rising rents (a studio apartment can run about $1,500) as factors that make Chicago tougher for people without financial cushion.

What new real estate strategies is Lisa currently exploring?

She's exploring reaching out to motivated sellers who currently hold 2-3% mortgages and may have urgent reasons to sell, and she's also looking into land flipping, though she notes land flipping requires some capital. She emphasizes that whatever the strategy, you need deep knowledge of the market and the numbers have to work before buying.

Resources and links

Lisa Rosenberg’s Email Address: lisaterracina.rosenberg@gmail.com

Full transcript

Lisa Terracina Rosenberg (00:00)

There are properties on the south side of Chicago that have been renovated. They’re not super fancy, but they’ve

had the work done. Or if you want to do a gut job and you have the capital to do that, that’s what I’d like to do. That’s what we did with our ⁓ historic renovation. It was gorgeous. It was stunning.

Dylan Silver (01:52)

Hey folks, welcome back to the show. Today’s guest, Lisa Terracina Rosenberg is a Chicago based real estate investor. She brings a unique background as both a chemist and experience operating a high end imported linens brand in Chicago, combining analytical thinking with hands on business execution. Lisa, thank you for taking the time today.

Lisa Terracina Rosenberg (02:13)

Thank you very much for inviting me. I really appreciate it.

Dylan Silver (02:16)

So I’d like to start off at the top of the show by asking about transitioning into real estate investing and how real estate investing played a role in all of the business that you’ve been a part of.

Lisa Terracina Rosenberg (02:28)

Well, I was born into the real estate business because my parents own both commercial and residential property. So even as a small child, ⁓ I knew the tenants and my parents would give me responsibility in our businesses. so ⁓ then later when my parents became older, I took on more responsibility, collecting rent, managing, doing repairs, so forth.

And it was a way to live comfortably. And ⁓ I think it gives you a lot of freedom. I think that’s what I miss about it is currently I’m working for somebody else, but I’m also working for myself. I’m a strategic marketer. I’m an investor and I’m an entrepreneur. And what I did in my business at Arrel Fine Linens was

the marketing and PR. So I’m a people person and I’m all about making connections with people. It’s actually one of the reasons why I’m here today because as a marketer, what you want is visibility. And if you want visibility, this is one of the best ways to reach other people. And ⁓ when I had my business, we would frequently be asked to speak at the trade shows and it’s just a great way.

to expand your audience and meet people that are like-minded, honestly. And that’s where you find your opportunities, is being in the right community.

Dylan Silver (03:58)

What do you look for when you’re evaluating real estate opportunities specifically? we’re talking about Chicago, what type of things are you looking for to identify a good opportunity?

Lisa Terracina Rosenberg (04:10)

Well, there are a lot of good opportunities in Chicago. The only question that I have is I wonder about what the tax situation might be going forward because the state of Illinois has some serious problems with their pensions and the schools. And I don’t know if they’re going to find a way out of that. And then a lot of this woke thinking ⁓

I think crime is a huge factor, all right? But I’m not super intimidated by it because I invested in Wicker Park when nobody was investing in Wicker Park, which was 1983. And I bought my property for $80,000 and I sold it for 1.5 million. It took me a while to do that. Like right now where I think the opportunities are in Chicago are on the South side, the South and West side,

like by Garfield Park.

places like that. They’re a little iffy. Now, the thing is that I’m at an age, I’m 71 now, and I want to be in familiar territory. When I was in my 20s or my 30s, I went into Wicker Park and it was a sketchy neighborhood. When I would go to the grocery store one block away, one street west of me, there would be literally 300 people on the street. I was the only white person.

And in fact, the whole neighborhood was kind of run by feral dogs that would make groups. And over time, that neighborhood thrived. Now, there’s been so much development in some of these bad neighborhoods, but they still have the crime. But over the course

Dylan Silver (06:36)

How important is proximity when we talk about investing? There’s a trend right now where people are doing more remote investing, even across state lines, but there’s of course great value from being able to go and touch the properties and walk the properties and go to them on a potentially weekly basis if there’s something that needs to be addressed, right?

Lisa Terracina Rosenberg (07:00)

I agree with you. think proximity is very important. Now it depends on what kind of real estate investor you are. You know, I am like right now, not really owning a home or anything. I want something that’s going to provide me with perhaps some passive income and a place to live. That is one thing, but I mean, we could do another way and just

stay where we are and invest in properties, but there are advantages to living in your property, especially if you’re first time investor. So since we’re starting out this way, ⁓ but I think proximity is very important ⁓ because it’s hard to manage things. mean, honestly, when I had a tenant problem, maybe my ⁓ was to not hire management property, but I didn’t know of a good management property.

And some of the people that offered to do that, I did not really trust them because I didn’t. They were people that wanted to get the property. So I was concerned about somebody like that devaluing things or I don’t know. ⁓ I can’t really change the past. I can only go forward, right? ⁓ But I think it just makes it like if you’re starting out, it’s

easier to deal with things, easier to deal with people. Now, some people don’t want to deal with people. And if you’re that kind of person, then a management company is the way to go and find a good one. But we always dealt with our tenants and we could observe if they were doing something wrong. Okay, so I went on a trip to England once for five days. had the residential property.

I came back, I had a lady there that would keep an eye out on things for me, right? One of my tenants. And she calls me up the day after I get back from England, I’m still like, you know, zombied out from the time change. And she says, did you hear what happened? Like, no, what happened? There was the police was here at three o’clock in the morning. And I heard this huge sound. didn’t know what it was.

All right, long story short, I go to the property, I go into this apartment, I look at it, it’s abandoned, it’s filthy, it’s disgusting, and I see it’s on the second floor, and I see at the window that the screen has been cut. I look out the window and I see a ladder going.

up to the second floor outside the window. And the refrigerator, which I had purchased right before the tenant had moved in, looked like it had been in a car accident. So I don’t know what happened in there, but I was called my husband at the store and I’m like, I don’t know what the hell happened here. And he says to me, I know what happened. She locked the husband down and he tried to climb into the apartment with the ladder.

right.

When you’re on the premises, you see stuff like that. When you’re miles and miles away, you can’t deal with it. And so that’s the advantage that you can nip things in the bud.

Dylan Silver (10:49)

What’s the biggest error that you see people making when they’re investing in real estate in Chicago?

Lisa Terracina Rosenberg (10:50)

But also there’s another factor with proximity. Well, I just want to say this one thing. To

know the lay of the land. You need to know the lay of the land. And if I go invest on the South side, I don’t know the lay of the land, but this area where I am in Logan Square, in Wicker Park, and I know the area block by block. And when you’re in a big city, a block can make a big difference.

So I’m more comfortable with that and that’s where I want to invest. I want to invest where I can see my bricks and mortar, touch and feel, deal with people directly.

Dylan Silver (11:27)

No question, that ability to be able to have proximity and like you mentioned, to be able to deal with people directly is a huge advantage versus having to hire that out or having to do things over distance without boots on the ground can of course be challenging. I would like to pivot here, Lisa, and ask you about Chicago as a whole and investing in Chicago can be tricky, right? You’ve got aldermen and you’ve got different areas of the city. For folks that are looking at investing in Chicago,

What general feedback would you have for them as they’re getting started?

Lisa Terracina Rosenberg (11:59)

Well, you have several things going on right now. First of all, you have the Obama Library that’s going up. And all the areas around, you know, Garfield Park, they’re already starting to get gentrified. So that is going to continue. You know, the more people you have, like when you have just one gentrified house and 99 % of them aren’t there, you’re like a target, right? But, you know, people start feeling the comfort and I think younger people are not.

quite so concerned. And honestly, crime is random here. It’s terrible though. It’s gotten worse. And I honestly question like, should I, should I not be in Chicago? I feel like Chicago is a fantastic place if you’re in financially great shape, but maybe not so great if you’re not. And you know, the other thing too is you can, you can live on a small income.

Okay, you know the problem is rents have gotten very high Everything’s gotten very high high Chicago used to be a very affordable place It isn’t affordable, but it’s more affordable when I hear about New York or I hear about California Where I’m hearing that people have to put down like six months deposit on a rental property. That’s crazy, you know, um

Dylan Silver (13:16)

Yeah, it’s true.

Lisa Terracina Rosenberg (13:18)

It’s gotten like a studio apartment can be like 1500 bucks. And if you’re not making very much money, that’s not so good. But here’s the thing. I need money because I don’t want to just live and exist. have ambitions and it takes money to do stuff and it’s slower to do stuff when you don’t have money. You know, like that is my regret right now. ⁓ There’s a lot of great areas.

Dylan Silver (13:37)

No question.

We are coming up on time here, Lisa.

Any new projects that you’re working on, and then as well, what’s the best way for folks to reach out to you?

Lisa Terracina Rosenberg (13:49)

The best way to reach out to me is through my email. Let’s see. I’m trying to think. I guess my email, is LisaTerracinaRosenberg, it’s lisaterracina.rosenberg@gmail.com.

You know, put in the notes, podcasts, real estate podcast, so that I know who you are. Or Dylan Silver, you know, so that I know who you are. But what I do now is I offer marketing, I can do content creation, I can negotiate for you. I have a lot of skills. Having run a business, I am good at like providing operational advice and so forth.

⁓ Also, we have people that are interested in investment. So if you have something that you’re looking for, right now, this is one of the things that I’m exploring is that I’m thinking there’s a lot of people with 2 % mortgages, 2 and 3 % mortgages. And out of that pile of people, there are people that want to sell their properties

and they may have a reason to sell it urgently. And that is one of the areas I’m exploring.

One another one is land flipping, but you need a little bit of money for that. I’m looking for an opportunity of somebody who’s a motivated seller. What were the thing is with my husband’s. ⁓ So you have to be prepared when you have the money and in order to do that. And that was something that I was did when I was younger, when I bought my first property, you have to know the market. So even if you’re not buying.

Currently, you have to have a really good knowledge of what the market is, what the upward potential, what the income potential is. It’s all about the numbers. If the numbers don’t work, you shouldn’t buy it. ⁓

And ⁓ right now, like

are properties on the south side of Chicago that have been renovated. They’re not super fancy, but they’ve already had the work done. Or if you want to do a gut job and you have the capital to do that, that’s what I’d like to do. That’s what we did with our ⁓ historic renovation. It was gorgeous. It was

Stunning. I mean, I had, yeah.

Dylan Silver (16:53)

Lisa, thank you so

much for joining us today. Thanks for your time. Thank you for coming on the podcast today. Thank you so much.