Would love to chat more with anyone here about that business once I get through tax season!

Worst case maybe a trailer/food truck pop up in addition to the seasonal businesses that Henry mentioned.

There are only one or maybe two that don't require seasoning, only source.Stephanie 

May have to season 12 months.

It's critical to ensure the conventional lender doesn't have any seasoning requirements as that could potentially ruin the deal.

Another big consideration is seasoning requirements.

I knew that different lenders had different rules (particularly around seasoning), but I really like your explanation on overlays.

Hey Bigger Pockets Fam,My colleague and I @Garrett Gatton are looking to break into the Florida market, specifically around Naples, FL for seasonal and short term rentals.

Can any of you more seasoned investors recommend additional reading suggestions? 

I have signed rental contracts for which I had to process refunds, have realized loss of 3 months of income so far with high season (January - April) rentals all canceled, and am going to be losing about 2X the income of the supplemental coverage limit.I know it's the insurance company's job not to pay and to estimate and undercut as much as they can.