Best to have a month to month lease or one with a start and end date if you want them to leave on a specific date, that lets you move to eviction if they don't pay.

So my question is: if I wanted to save on the recording costs, keep the deed for my records, proactively pay taxes as they're billed (would coordinate with the company I buy the CFD from), then work with the borrower to get the deed recorded under their name once they've paid off the contract--am I putting myself at risk? 

Which that benefit alone ends up paying for itself in the long run.

Trust but verify.

Or, depending on the interest rate paying off the student loans.

Money is to pay the bills.

Taxes wise I have opened up a high yield savings account and putting money into it in case I do end up owing taxes next year, but what do I need to be saving as far as forms, I don't have the tenants on a lease yet since this is my primary on the mortgage, but I am giving them receipts when they pay rent every month and keeping those saved.

This particular investor used to be my middle school English teacher, and wanted to do a deal that would pay him every month so that he knew he and his family would be taken care of even if something were to happen to him.

I would pay Wealthability if I see that the proposal would indeed save us more than we pay for the fee. 

These lenders might be more open to financing smaller amounts, especially if they see potential in your project and trust your investment acumen.Seller Financing - In some cases, the property seller might be willing to finance the purchase.