Check if your management team has a slick process in place or if they can up their game.

If you do decide to take the leap and buy something just keep those (2) options in mind.You can also use a "Bank Statement" loan where the banks looks at 12 or 24 months of your business checking account and will add up all of your gross deposits and use 75% of the income as an annual salary.

To be honest it's a strategy you should check out if you haven't already.

I have checked the number of reviews across all the bnbs on the island and I can see that the slower months are between November and February, as mentioned by @Lake Lutes (thanks btw!

How often are you having your pool checked and cleaned for your STR?

I send out check right away, but thinking of asking him to move to monthly or bi-monthly payments to streamline the process...Any thoughts would be greatly appreciated!

does this LLC you speak of own the property and who has signing authority you need to check that if you have it then sell the property and sue the flipper.

My 'due diligence' is just about checking out a 'single house.' 

Generally you want to get to at least $100k in loan amount with $75k absolute lowest for both hard money and DSCR - probably your best bet is to finance with cash or private money investor/partner on the first few projects until you build up enough capital to get to those higher amountsPS - you mentioned a lot of reading and learning on this, on the chance you didn't see this article, check this recently published BiggerPockets piece I did on your exact topic - Pros/Cons/Options of financing BRRRR strategyhttps://www.biggerpockets.com/blog/brrrr-loans-what-are-the-...

Just another "spreadsheets aren't real life" reality check.