However, it is an interesting point since although it's not the last month of occupancy it is the "last month" of the current contract - they could claim to just want to re-pay it at the start of the new contract.

Welcome John, I would love to share some options with you here in SWFL.

Some other investment loan programs allow gift funds, so there are options out there besides conventional financing. 

I have purchased a property on cash using my HELOC and I was wondering if there are options to do the following:1.

You will then have a few options with that rent money....you can put it into principal or you can start saving it to purchase yet another property.

Calculator should provide amount of conversion  tax payments needed, one or multiple conversion options,  Medicare IRMAA impacts, various investment percentages of Roth growth vs IRA growth, and RMD amounts with associated tax bill.I’ve seen numerous CFPs hawk their services for $5,000 or more.  

Test them out, if they aren't good try another option until you find the right fit. 

Now a permanent buy down option (where they just pay points in a traditional manner) can solve some minor DTI issues.  

OK, I would urge you to be very, very careful here...Certain operating expenses are paid monthly from lender escrow, so it's easy to assume that any costs not paid this way are somehow "optional."

Considering your situation and goals, here are some insights to help you navigate your options:1.