The STR I purchased before the wedding was fully paid for before the wedding.

Additionally, you want to invest in making sure your property stands out against similarly sized ones in the area with tasteful decor, themed rooms, game rooms, etc.

We also had a party of 8 request to change their April weekend for an October weekend as the bride and groom rescheduled their St Augustine wedding. 

@Bobby English I would echo the theme of "ask a different bank"....I have not done any "non-conventional" financing as of yet, but have had several discussions with banks around town regarding some different ways to finance now that I am self employed and by far the best terms and most understanding of "the deal" has been my local Telhio credit union here in Columbus OH. 

We are recording a podcast Wed with J Scott, myself, David, and Brandon to talk about the economy and it's likely impacts on real estate.

The serious about negative cash flow isn't connected only to this theme. 

Andy, if you haven't already, sign up and attend the webinar for Wed.

With the Coronavirus causing Florida's theme parks to contemplate closing, there is a risk of Florida heading for a downturn.

We can refinance if we need to buy a big ticket item (wedding, college). 

Your CPA has a narrow view that is specific taxes and accounting, I'm not diminishing his knowledge or advise, just giving a different view on a broad and complex theme.