Not all credit unions give out Home Equity Lines of Credit (HELOCs) for investment properties, so check if they're down with that.

If not I would double check your rent against the market.

I'd also check if the utilities are still in the original tenant's name. 

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.

You can also check meetup.com or search facebook for real estate investment groups, clubs, or meetings in your area.

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

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!

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

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!