You never know when the peak or the valley is. 

SINGLE FAM Scenario 1: The single family home 3bd/2ba home could get me $27K/annually via airbnb ideally without considering non-peak season and I'd want this single family only for short-term rental purposes only; not long-term.

STRs that are not the absolute peak performers are already having issues with vacancy, and AirBnB recently changed their platform so that only the absolute cream of the crop units (five star resort-level luxury units with thousands of perfect guest ratings) are getting promoted.In a nutshell, STRs are a lot more work, require a lot more expertise, and are a lot less reliable/secure than traditional long term rentals (all other things being equal).Plus, house hacking a long term rental will give you invaluable experience in how to analyze, acquire, and a manage a property that you can then apply to doing a STR in the future (if you decide you want to go that route).Start with the strategy that is the easiest, simplest, and most likely to succeed (house hacking), and then gradually build up to more advanced strategies (like STRs, BRRR's, etc.) as you gain experience.Good luck out there!

I have financed when I had the cash then used the cash when speed or condition wouldn't allow for a mortgage. 

But there are also less speed bumps along the way in escrow, setup and operations.

Would you rather buy at the peak or the bottom?   

lol  Again, IF no attic in that space, You could still install the Ridge Vent itself on top of that 12ft peak area, just not cutting out the decking there (not cut slot under the vent!).

(Specifically Emerald and Forgotten Coast of Florida)We are still in a peak market.

This road is residential and the speed limit is 30 but it still worries me about safety.

Also, it will be good to get preapproved for your loan, so you can move with speed when you find the right property!