All Forum Posts by: Aaron Zimmerman

I would echo @Jonathan Greene. All of the people he mentioned are great resources to the Chicago real estate community. To add, I would include @John Warren and Brie Schmidt here as well.

I would highly advise against purchasing a property within an S Corp. If the property appreciates, you will have to pay tax if you move it out. There are basis limitations that affect whether you can take losses or not.

There a lot of great CPAs on here that may be able to assist you.

On a go forward basis, I would not own real estate within an IRA. Like you indicated, there's a lot of minefields. Also, real estate is already tax advantaged so no need for the IRA.

I would think selling would be the best option so you can move on from the property and then invest elsewhere (not in an IRA thereafter).

To echo what others have said, find another accountant. There are plenty of better ones. That is terrible advice!

To add to @Ashish Acharya, I would recommend using your retirement funds for notes that earn a nice interest rate, if you're into self directing.

Given that you want to purchase a short term rental, I'd highly recommend not doing this within an IRA/401k.

You will pay a lot of money if you cash out now. Another option might be roth conversions and then accessing that money in 5 years from the date of conversion. 

I would recommend connecting with people in the Chicago real estate circles. There's lots of groups such as the Chicago Friendly Landlord Group, Chicago Multifamily Club, Straight Up Chicago Investor, etc and would recommend posting there.

There's a lot of real estate CPAs in the Biggerpockets forums. I'd recommend reaching out to a few and interviewing them and seeing who you connect best with. BP also has a tax professional finder as well. 

 Given you're in Texas and don't have a state tax return, it really opens you up to work with providers nationwide. 

 Kris - Welcome to the forums. 

Ultimately, it's up to you and your personal comfort. Do you have free time to look into buying properties/can you make it a priority? I can imagine with having young ones, it can be a lot!

You're likely looking at a 25% down loan for a non-owner occupied. 

There's many other options in real estate such as syndication and note investing depending on your level of involvement. 

What areas are you looking to buy in? Are you looking for cash flow immediately or can you wait?

To me, it's always best to start earlier than later. I'd expect prices to continue to appreciate, so the longer you delay, the more expensive things may be. 

Happy to connect as well as I'm based in Chicago. I'm an investor with a couple properties as well as a CPA. 

You’ll want to get loans from local banks and credit unions but you may run into issues with more limited features. That said, I prefer Chase since they have all the functionality you’d need. 

BiggerPockets is a great resource for finding real estate CPAs. There’s about 20+ on here. I’d recommend looking at some of their previous comments and posts, seeing how well you align and interview a couple and choose one.

May I ask what your budget is? Are you looking for tax prep or tax prep and advisory?