Banks, particularly smaller banks who provide real estate loans are increasingly focused on their borrowers maintaining depository relationships.

I do relatively well in my day job by today's standards but my hourly rate for self managing is closer to that of a surgeon. 

People don't read STR descriptions you see this alot with international properties where people expect US standards.

I am hopeful they will want to work with me to get things repaired and updated to validate appropriate rent increases.

It's a riskier loan given you do not carry a social security, no US credit & no experience.Due to increased risk comes mitigation (Lower LTV & Higher Rates)

That seems like an expensive roof - does it need to be completely torn up and rebuilt to hurricane standards?

My mortgage increased earlier this year as my home owners insurance went up due to the company closing and my escrow didn’t have enough to make up the difference so I’m kind of pay check to pay check right now.

I looked back at my tax returns when I was doing the conversions from my traditional IRA to my Roth IRA and realized I had converted up to the limit of my standard deduction allowing that amount to be tax free, but the excess above that that I converted each year was at the lowest tax bracket, so while I did convert some money tax free each of those years I DID IN FACT pay more than a few cents in taxes on the amount above the deduction.  

You can even work out a base 5% and they get additional bonuses for beating the planned vacancy rates to allow them to achieve 8% or 10% of gross rents which is industry standard. 

When you mentioned that you don't have a lot of money to start with, I'd recommend focusing on increasing your current income and decreasing expenses.