Usually seasoning is 6-months or more (depending on the program) and the lender will want to see leased units. 

Disclaimer: I'm only one deal into the business, so please listen to the more seasoned people ultimately.

That transition becomes messy and costly to many investors as they didn't take into account low appraisals, seasoning periods, LTV restrictions, etc...

Not as good as we were buying, but good enough to execute most of the sales before the world started unraveling.The best decision we made during our disposition process was seeking out seasoned agents who were specialists in their market niches and letting them work their magic in their market specialties.

After doing this, I then run the property through Airdna.co and/or Mashvisor.com  Both of these tools will give you projections of what type of rental rates, price per night, bookings, occupancy, seasonal variations, etc. 

Finding an older house to rehab in those markets would be a better option in my opinion.  

You could loan on that, let the $ season for 3 months in the borrower's account, then record the lien on this asset  or the original one as a 2nd.  

I run a couple of other businesses that vary based on seasonality (Turo and RV rentals) so am familiar with the fact that pricing will change as demand changes.Are there good resources our there (or consensus from the group) as to where 2200 sq ft with a hot tub and 15 minutes from some of the best beaches in FL should price? 

Connect with seasoned real estate investors, mentors, and professionals in the area to learn from their experiences.

(exactly) If it is older and needs attention, many times you may be able to do a "coating" on it, instead of replacing it.But a coating, or even possibly doing a 2nd layer, all depends on what is there and it's condition.