I know taxes and insurance have gone up a lot in that time so I understand that problem but the solid rent increases in that time have been able to cover most of that (at least for me it has worked out).

Florida scares me with insurance issues and constant threat of hurricane damage.

Chat with them, and ask them where they find their guest (Airbnb, Furnished Finders, Insurance claims, etc).

Even when the deed is recorded you will be unable to obtain title insurance for at least a year from the date the deed is recorded.

Make sure you have the right property insurance while the property is being worked on and an investor friendly lender or local credit union can help you refinance or get a HELOC.To Your Success!

Add another $300 or so for taxes and insurance and you're at $2465 PITI. 

Payment to the bank is $4,311 (includes escrow/insurance), total monthly rent $5,600, which leaves me roughly $1,300 monthly after expenses.

Can anyone provide insight on the average cost of insurance for Airbnbs with pools in the Boston area?

Florida did just have back to back hurricanes but a proper master insurance policy and coverage usually covers that type or perilYou are facing a declining cash flow situation which is due to the HOA fee's so while there is still a profit and you have equity sell and look for a 2-4 units.

This will help you determine if it’s financially viable.Insurance: Look into insurance for both the mobile home and your land.