I'm looking to pool 5-10 investors together to form what is basically a small-scale REIT.

Could we do a portfolio loan where we all pool in equal shares of the required down payment?

Yes the HOA will add to your expenses, but you also don't need to pay for fire insurance, outside maintenance, long-term capital improvements such as new roof, water, trash, and whatever is in the community such as a pool or gym.

It seems that a guest was, for some unknown reason, attempting to move a slate pool table. 

A lot of people are using this money to enjoy their summers and go to the pools and vacation and whatnot.

The safest bets for investor popularity are usually the Sunny Isles, Brickell, and now Edgewater submarkets.

I feel kind of like a little kid standing at the deep end of the pool tentative about jumping in.

I'm looking at somewhere between $130-$150 per night for a 5 bed home with a pool and hot tub.

I'm not savvy, lucky, or connected enough to have found good deals on residential multi-family though and right now I feel like SFH offers the easier\faster exit plan if I need to sell in a hurry because your buyer pool is exponentially larger. 

The buyer pool - consisting of debt addicted institutions and high net worth individuals - will chase deals harder than ever before.