I sent you a private message and would love to assist you here in your house hacking search.I am very familiar with all three of those markets and feel confident I could assist you in finding a great opportunity in the next 60 days! 

If he doesn't do biz structure or contracts,  I bet he'll have referrals.  

consulting  a civil right attorney is probably your best bet.

tend to believe everyone is motivated by money; people who are lifestyle motivated think everyone is motivated by the least amount of time expended; people who are risk adverse can’t believe other people are willing to “bet” on outcomes even when the odds are clearly in their favor. 80% of the time (IMO) people who make decisions we disagree with are not making stupid, ill informed decisions or being “tricked”; they just have motivation, needs and desires different that our own.  

In that price point, you'll do well to look in Seminole Heights.Value add will always be your best bet for better ROI, but out of town buyers usually will want as close to turnkey as possible.A pool will add 30%+ to your ADR. 

I haven't seen any online forums but if there is one, I bet it's a Facebook group. 

And when Google seeks to monetize it, I would bet we see similar fees.

You bet.

Would the best bet be for me to just park a chunk of that money in a high yield savings account until tax time?

Personally, I'm betting my own money on it, looking for investments now that our inventory has creeped up to about 4 months supply, which is still pretty low compared to most markets.