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.

Seems odd as this would be a business expense for my business.  

When you do the turnkey offerings to completely new investors like that, you're going to end up working with a lot of inexperienced investors who blame the turnkey operator for things that are a normal part of the property management business.

I could use some help, and likewise would love to bring business to those in the community here.1.

I know you can do one per but that would be a hassle if you scaled your business.

@Matthew McleanBigger Pockets is a great place to find an accountant specializing in real estate taxation.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 specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your accountant remotely to expand your options.I would also recommend looking for an accountant willing to work with you throughout the year.

Policymakers, government officials, and business leaders can leverage this analysis to craft targeted strategies for fostering sustainable growth in the metros that drive America’s economy.Read the FULL STORY HERE

I have recently been made aware that I get straight to business without really concerning myself for the sellers side of the story and when you have the sellers problems, goals, etc.

Heck even culinarily the restaurants that are popping up are impressive (which I take as a great sign of the people and businesses that it's attracting). 

Courtesy of the video, criteria to consider include Deal Type, Management Plan, Business Plan, Financing, Asset Class, Ownership Structure, Property Class, Location, Purchase Price, Rehab Costs, Risk Target, and ROE Targets.