All Forum Posts by: Aaron Zimmerman

Yes. As others have said, you're eligible for the section 121 exclusion to exclude $250k gain if single or $500k if married. This is a significantly better result because you won't be paying taxes on the gain! 

Just make sure you live in the property for two of the last 5 years! 

@Emanuel Escarpita would be a great resource to discuss flipping. He's very active in the Chicagoland area with his flipping business. 

in addition, I would recommend listening to the straight up Chicago investor podcast for local insights that you won't get anywhere else.

@Emanuel Escarpita would be a great resource to discuss flipping. He's very active in the Chicagoland area with his flipping business. 

in addition, I would recommend listening to the straight up Chicago investor podcast for local insights that you won't get anywhere else. 

Welcome to Chicago! I would recommend listening to the straight up Chicago investor podcast for local tips and attending local meetups.

 I'm a former house hacker and real estate CPA in Chicago. I'm down for a phone or video call and happy to help you out. Feel free to PM! 

I would recommend going to local meetups such as Chicago Multifamily club or Chicago Real Estate Investors

I think the biggest win is 100% bonus depreciation being made permananent so will touch on that. I think this will be a boon for syndications and STRs in particular as there are now more tax benefits to be obtained in year one. I didn't see any changes on class lives (it was Under 20 years or less for bonus depreciation eligible items) and typically roofs, hvacs etc are only eligible on commercial (39 year property) as qualified improvement property, not on residential property.

It also makes buying at these levels easier if you can do a cost seg study and offset income. It's an important reminder that wealth in real estate is built 4 ways (cash flow, appreciation, depreciation, and tax benefits). 

Congrats on your success!!

You're well ahead of the game for someone your age. I would encourage you to save as much money as you can and try to work during the school year if possible. This will set you up nicely for purchasing your property. You want to make sure you have adequate cash reserves. On a $350k property, you realistically need upwards of $15-25k including reserves to get started. You could do with less but realistically there's no reason to stretch yourself thin at this point during your RE investing career 

I think STRs make a comeback with 100% bonus depreciation being back on the table for 2025 and going forward. Whether it's the right decision for them or not, TBD. But that's my take regardless of market. 

1. Why do you need 20% down? There are loan programs available for 3-10% down. I would encourage you to review those options. 

2. do you have an option to take out a loan from your 401(k)? This is a much better option as you're paying yourself back. With interest rates being higher, you would likely be paying yourself back at least 8% as opposed to a bank. This also avoids the tax hit assuming you're able to pay the loan back.