All Forum Posts by: Steven Hamilton II
Steven Hamilton II has started 25 posts and replied 5110 times.
Post: CPA recommendations in the Chicago area?

- Accountant, Enrolled Agent
- Grayslake, IL
- Posts 5,272
- Votes 2,325
@Lance Lvovsky thanks for the mention.
I'm in the North Suburbs near Gurnee; however, I meet with clients worldwide. Reach out if you have any questions.
Post: 1031 exchange - taxes and not matching debt

- Accountant, Enrolled Agent
- Grayslake, IL
- Posts 5,272
- Votes 2,325
Yes, there is what is called mortgage boot. If you acquire for anything less than you sold minus allowed selling expenses you will be subject to capital gain first.
You need to review this with your accountant ASAP.
Post: CPA/ Tax/ Accountant Recommendations in SWFL/Florida

- Accountant, Enrolled Agent
- Grayslake, IL
- Posts 5,272
- Votes 2,325
Originally posted by @Natalie Kolodij:
If you guys are open to working with someone remotely
@Steven Hamilton II is an amazing EA and has an office in Florida (but I think it's further north than Cape Coral/ Ft. Myers)
He's specialized in REI, he's an investor, super active here on BP. I'd reach out and see if he's accepting new clients.
Thanks for the mention. I'm in Ft Meyers on a regular basis. I know all of the IRS agents at that office on a first name basis.
Feel free to reach out if you have any questions.
Post: Real Estate Accountant

- Accountant, Enrolled Agent
- Grayslake, IL
- Posts 5,272
- Votes 2,325
Post: CPA vs DO IT YOURSELF

- Accountant, Enrolled Agent
- Grayslake, IL
- Posts 5,272
- Votes 2,325
Originally posted by @April White:
Hello Everyone,
I just recently started a business this year to do LTR, and started fixing up a little house in the back of the property as well but ran into plumbing and electrical issues that cost more than expected (already in the hole by $5k prior to plumbing & electrical) while I was trying to get the main house rented. Unfortunately, I wasn't able to get a qualified tenant through my property manager for 6 months so I fired the property manager to decided to furnish the home as a STR for roughly $2800. I started my STR in Aug 2018 and it's currently bringing in $1800-2200/month (will most likely increase as I reach super host status and increase my rate giving me closer $3k compared to current) but I'm still negative in cash flow by $400. If I didn't run into issues with the little house I was going to rent it out for $900 a month furnished.
Now my question. Prior to starting my business I did my taxes myself via TurboTax and never had a problem. I hear a lot of investors use CPA, but if you can’t afford a CPA what would be the best route to take to file your taxes?
I already know I need to do a 1120, and a 2553 to try and get an S Corp. election (I know usually bigger companies use this but I plan to expand and it would be nice to already have everything in place) but my biggest concern is the write offs for starting a new business, net loss, and whatever else can be deducted.
Does anybody have any suggestions for my situation or can give testimony on what software they use other than a CPA?
Thanks!
April
Honestly over 90% of tax returns I review have some type of issue on the return. Are you familiar with balance sheets, accounting and tax law? If not you should not be preparing your own Form 1120-S. Most owners of real estate and small businesses should not be preparing their own tax return. A high number of "preparers" screw them up as it is.
Don't get me wrong I love TurboTax. The amount of work it brings me due to issues from those using it to prepare their tax returns is in the six figures.
Post: Opportunity Zones Research

- Accountant, Enrolled Agent
- Grayslake, IL
- Posts 5,272
- Votes 2,325
Depreciation recapture is another matter. You have to be quite careful. I agree commercial would be easier.
A regular flip would not qualify as it is business income, not capital gains.
Post: Roommate Rent -how to claim that income?

- Accountant, Enrolled Agent
- Grayslake, IL
- Posts 5,272
- Votes 2,325
First, you need to consult them or an attorney on the ownership situation. You can do a quick search on "house Hacking" and they will show you exactly how to account for everything.
Post: Irs 170 exchange

- Accountant, Enrolled Agent
- Grayslake, IL
- Posts 5,272
- Votes 2,325
It is very much like donating appreciated securities. You can donate appreciated real estate. My only issue is it seems like they are inflating values and issuing letters that have certain requirements namely being the easement cannot be contingent on the deduction being allowed.
Post: Seller Financing and Taxes

- Accountant, Enrolled Agent
- Grayslake, IL
- Posts 5,272
- Votes 2,325
Go here: https://www.irs.gov/publications/p537 Then search for Worksheet A.
Post: Looking for Real estate savvy CPA in Chicago

- Accountant, Enrolled Agent
- Grayslake, IL
- Posts 5,272
- Votes 2,325
Happy to help of there are any questions.