I guess it ultimately depends on your end goals.

I think ultimately there needs to be some commonplace legislation at the state level to make sure its not just people buying up houses to rent out like hotels willy-nilly, but also that its not infringing on an individual homeowner to rent out a room or apartment in their home.With some 40,000 AirBnBs in Florida generating 10s of millions of tax revenue I don't see how Florida can turn them down.

I would ultimately like to refi, get the money I have put into it back, and use that money decrease my overall debt to income.

But because we don’t depend on our real estate investing income for survival, if there is a market correction that causes a decrease in home values more than 20% and rents to drop 15-20% also, then our cash flow may temporarily go down to zero.

So if Biz #1 has 20% of the properties, Biz #1 pays 20% of the expenses.That being said, I'd be open to simplicity just because ultimately it's only a difference of a few thousand and we both don't care much.

Your ultimate goal is to achieve maximum leverage and be owed enough money to justify taking her to small claims court.

Am I missing out on serious compound interest effects that will hurt me down the line, or is it smart to make sure I have the necessary cash if house hacking is the ultimate short term goal?

Check out: The Ultimate Guide to Grading Cleveland Neighborhoodsand James Wise who made the map if you haven't gotten around to it already. 

Check out this Ultimate Guide on wholesaling, it can help a lot https://www.biggerpockets.com/renewsblog/2015/01/31/ultimate-beginners-guide-real-estate-wholesaling-2/?

A good primer on tax-advantaged accounts (IRAs, HSAs) can be found on the Mad FIentist site (https://www.biggerpockets.com/forums/846/topics/563476-ep-18-accessing-retirement-funds-before-59-1-2-w-the-mad-fientist, https://www.madfientist.com/ultimate-retirement-account/).My background: I worked for many years as an independent contractor through a temporary help agency.