We bought land with an ocean view, built and furnished for a total investment of about US$300,000. 

Wells Fargo initially quoted $1M value at for the house so they said $5.5K for the county tax (.05%) and $13.1K  (1.28%) but a total of $18.6 in taxes but that seems really high

Obviously with the opportunity to opt out. 

I currently use a PMS (RentRedi) to manage my long term tenants (2x house hacker here with 11 tenants in total) which has worked very well.

Here's your challenges:1) Owner is either lying about there being no leases, is totally incompetent or, the worst, is a slumlord trying to take advantage of tenants.--- Which means he's trying to take advantage of you!

If you acquire the property in the middle of November(Assumption of November 15th), you will need to clock in about 2 hours a day.You might be able to log in a lot of the hours as you furnish and rehab the property leaving you with 30-minutes / 1 hour towards each guest check in / check out.It is do-able but obviously, sometimes, the more time the better.

Obviously with doing your due diligence. 

So the total amount that should be paid will be rent for remaining days in month + security depositORrent for remaining days in month + next month + deposit - I don't know when would this situation arise.

Section 8 Homeownership Vouchers (TOTAL) DefinitionSection 8 Homeownership Vouchers refer to housing subsidies received under the Housing Choice Voucher homeownership option from a Public Housing Agency (PHA).Required DocumentationThe Mortgagee must verify and document the Borrower’s receipt of the Housing Choice Voucher homeownership subsidies.

Input new flooring, new HVACs and had it at a total value of $18k.