All Forum Posts by: Jake Shulman

You can always rent out room by room. You can also buy a house to live in, but make sure to run the numbers on it so that when you are ready to buy another deal, you can rent out the house you have to tenants. 

Preferably, you would buy a home that requires some work to be done under market price. Once you rehab the house, down the road you can refinance it and get some equity out. Then that equity can be used for a down payment on another house. 

@Jake Shulman: I can also recommend the Andersonville area or the area close to (slightly west of) the Thorndale red line station as a long term investment. It is relatively quiet, safe, close to the city and most importantly to the lake & lakeshore drive!

Perhaps the experts @Paul De Luca and @Brie Schmidt can also confirm if this makes sense. Cheers!

@Jake Fugman - ALL super great points that you can leverage as you go forward. I will  just add a few other pointers that I always ask my clients to ponder on: 

Before you start to invest, know your why in investing in real estate? What goals do you need to accomplish your why? Do you want cash flow versus appreciation? Do you need the cash flow now or can it wait? What is your appetite for rehab?

@Jake Shulman - Tons of smart people above have given you some great advice.  Figure out your purchasing power and then you get can figure out which area fits your budget.

I'll throw out some the neighborhoods I like and that seem to be in the path of progress.  Bronzeville, Washington Park, Kenwood, Portage Park, Hermonsa, Albany Park.....Honestly anything along the blue and red lines will always be good long term

@Jake Shulman you have a lot of heavy hitters who have already responded here with great advice. Chicago is literally covered with 2 and 3 unit properties, so I would start with where you want to live. Where is that? North side? South side? Suburbs? Generally speaking, you can find 2 and 3 units everywhere that was built up from the late 1800's up through the 1960's. Once you go west of 294 or north up to the north shore it gets hard to find the inventory as the demand changed more to single family homes. 

@Jake Shulman

In reality there are 2/3 flats in every neighborhood of Chicago, except that in the more established and trendy neighborhoods most of these have already been turned into condos or giant single family homes, so the remaining stock is very limited. You will want to look at neighborhoods adjacent to the most popular ones to find better deals. Apart from the ones mentioned I also have properties in Pilsen and Little Village, which have a lot of 3-4 unit housing stock.

People in this thread are right to say that a lot depends on your budget and the lifestyle you intend to persue. If you just want to reduce your rent payments and have someone else help you pay off your mortgage you can look just about anywhere. If you want to live rent free and cash flow at the same time you will need to get more creative and look for properties off the beaten path.

I agree with the neighborhoods already listed here. One thing I'd add is to find a great lender that can walk you through the different loan programs and where they apply. Once you have those, just start punching your pre-approval numbers into an MLS aggregator real estate site/app, select multi-family, and see where options pop up and drill down into the areas to see which ones you'd like to live in.

@Jake Shulman

As @Brie Schmidt mentioned Chicago is a very large area. You need to think about breaking down some of your criteria. 

1. Location

2. Budget

3. Type Of Neighborhood (A,B, C) I would avoid a D area. (Also do you want to be with in City of Chicago or suburbs)

4. 2 - 4 Flat This will depend on your budget & Location

5. What is your expectation in terms of Cash Flow/Equity In the Property? (Are you ok just breaking even or do you want to have cash flow while you live in the property)

6. How much work are you willing to do & Is that something realistic for you. That will depend on the condition of the property you can buy. 

This is a lot to think about but if you are going to buy and house hack might as well put some work in on the front end. So you can end up with a good outcome that will yield dividends for years to come. 

The question you asked is a good one but very broad. 

Start with Area Selection first and if you want the numbers to work you will have to look at B or C areas. A areas are very hot and cash flow will be very tight. Also depends on the condition of the property and if you have the willingness and ability to identify off market deals vs. MLS. MLS is very tight. Not that things don't come up but then you have to be ready to jump.