I am an out of state investor and in the past I have purchased my properties based on video walkthrough that my (trusted) realtor does.

the more units you have the less per unit per month.Like @Ryan Moyer mentioned, OwnerRez has a library of videos you can view and has a 14 day free trial, unlike Hostaway that doesn't have a free trial.

PRELIM LAND PLANNING- do a preliminary layout, please remember stream buffers, specimen trees, ANY jurisdictional waters (its a good idea to have you county water systems guy come walk your property with you to verify any jurisdictional water systems and what the required state and county buffers are for those systems).

Check their communication style - do they respond promptly, comfortable with video calls, and send regular updates?

Buying multiple lower-cost rentals would diversify income streams, or you could go for a short-term rental for higher returns if you can handle the management.

It''s like selling a bakery and the building, you have to value both.Arguably, the buyer pool is small, but maybe there is another operator close by, who would like to expand and leverage synergies.Hold up.......You got an offer of $200,000+ for a YouTube Channel that has 12 videos and 51 subscribers?

The upside to holding as a rental is, presumably, you have an income stream for a while, so you take reinvestment risk out of the picture.  

We give them the exact address, a video of what it looked like when it was bought, who did the rehab, what the rehab cost, what it rented for, a video of what it looked like AFTER the rehab, who did the loan (who the lender was), etc. 

I need to quickly and soundly and carefully determine how to regain some cash flow income stream, potentially utilizing two homes I own.

South Florida is a competitive market, and you'll need to do your due diligence on zoning, parking requirements, and other restrictions.I also made a quick video breaking this down in case you’re interested in hearing more details.