I would simply Google "legal restrictions for short term rentals in city X" or "short term rental permits in city X".  

Bret Kingcade - if 1-2 days off work is worth the potential money differential, then fight it.

You need to build a team (Legal, Title, Appraiser, Accountant) just like when buying real estate. 

I know it's a ton of information, but is there some sort of reference guide I can obtain that will guide me to the correct information I need to get started correctly so I don't get into legal trouble down the road?

@Braeden CobbBy using varied rental strategies, you can maximize the income potential of a 3-4 plex house hack.

Which is a bit like saying they will let the sun rise in east, because there is no legal ability to stop that given contract law. 

To that end, I look forward to connecting with investors, brokers, and lenders in Indianapolis and other Midwest markets to tap into your knowledge and discuss any potential triplex/fourplex buy and hold opportunities.

Or what seems crazy to me.Is it legal to create a 501c3 organization to buy investment properties and rent them out at fair market value?

In the end, if you do the math right and you are putting it on top, it would be better than losing time and potential money to interest payments if you have a loan. 

Michigan might be a bit easier to start with because you may have more knowledge about the local area and market trends, but starting there could potentially slow down your move to Florida.