Hi Davis,I live in NC but invest primarily in Greenville SC / upstate with my business partners. 

Hey @Keagan Scott, so I don't have any insight into Gary, IN but here is a blurb -"Those looking to rent out their properties for less than 30 days (about 4 and a half weeks) will have to get a permit, pay a one-time $150 fee, and have a city business license.

But investing is a decision business, do I make an offer?

I am here to create a business strategy that protects personal and business investments and mitigates risk,  procure a coach or mentor, and set up tax strategies to create long-term wealth for myself and my family. 

Shaun Shaun,I am a "specialist" and currently a business owner of a design and drafting company in CT. 

As good as offsetting all his W-2 / Business income?

Hi @Nancy Cho happy to connect and talk business.

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

Another thing, the threads move down the forums rather quickly because it's so busy, so the odds of your post being seen for long by very many people is minimal. 

In the latter case, I would still use QB to enter info provided by the 3P servicer and to maintain my general ledger for the lending business.