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

How do tenants feel about shared living spaces versus more private accommodations?

You bet.

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

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. 

If you have $100,000 in your brokerage account to borrow against, why not just use the money and secure a traditional loan, versus gambling with an unknown and variable future rate?

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

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.  

You can take ownership in 6 months versus 2 years in houses.