Starting out in Chicago Northside

4 Replies

Hello Everyone,

I’m taking Brandon and Josh’s advice from show #200 and hopping on the forum and asking this question.

I would like everyone’s advice on where to get started in real estate.

37yr old married male

Goal is to be financially independent by 47 need to generate 5k passive income to do so

Some savings 30k I could liquidate

Own SFH with 80% LTV

Narrowing it down thinking of buying a second home multi unit 2-3 flat

Also thinking of doing a 203k live in flip and rent out primary residence

Also thinking of buying a 2-3 flat with friends and doing house hack while renting out primary residence to get started

Would love everyone’s thoughts

Thanks so much ladies and gents I really appreciate your value and time

Justin Gears

@Justin Gears I love that you are taking action. You are in the prefect position to house hack in my opinion. If I were in your shoes, I would consider selling the SFR all together. You could feasibly pick up two house hack 2-4 units in the next year, and then you could pick up another 1-2 every year for the next few years if you were super aggressive. I have one investor client who did just this, and in 2.5 years he went from zero units to 15!

@Justin Gears Lots to think about here so I'm going to throw out some scenarios. One strategy depends on how much of the 20% equity in your SFH can be turned into cash after you pay capital gains tax. If the remaining cash is substantial then a 203K multifamily live in flip, using the BRRRR strategy would work. You could repeat this and eventually purchase a multiunit on your own.

If however there won't be much cash from the sale of your SFR then you may have to consider turning the SFR from your home to an asset; i.e. a rental. Live w/ some friends, then use the $30K to support a downpayment on a multifamily live in flip.

Originally posted by @Justin Gears :

Hello Everyone,

I’m taking Brandon and Josh’s advice from show #200 and hopping on the forum and asking this question.

I would like everyone’s advice on where to get started in real estate.

37yr old married male

Goal is to be financially independent by 47 need to generate 5k passive income to do so

Some savings 30k I could liquidate

Own SFH with 80% LTV

Narrowing it down thinking of buying a second home multi unit 2-3 flat

Also thinking of doing a 203k live in flip and rent out primary residence

Also thinking of buying a 2-3 flat with friends and doing house hack while renting out primary residence to get started

Would love everyone’s thoughts

Thanks so much ladies and gents I really appreciate your value and time

Justin Gears

 Welcome.  I'm also a 37 year old married guy.  My wife and I are investors in the city and own several multi-families.  

I think 203K and owner occupying a 2-3 unit is a great place to start!