Even if you have to pay a bit more now and have CF decreased, you will get the funds to continue deals and can reposition later. 

How much do I pay?

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.

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.

Landlord pays the bill.  

At the end of the day, it's still technically a Single Family Home with an extra unit to help offset expenses, but not a "true" investment property or legal duplex.Does anyone have any ideas on creative ways to finance building this (besides Refi or HELOC)?

Every multi out there right now for sale are occupied with low paying tenants.

We would NOT need to order a 1007 market rent report if we had either:1st months rent and security deposit2 months of rent deposits (canceled checks)If it’s a departing residence we could only use rental income to offset monthly payment (we couldn’t use extra income if 75% of the lease was 3,000 and mortgage was only $2,500 I couldn’t give $500 of income to boost DTI unless he has moved out of the home for some time and we have 1 year of history of being a landlord (which it sounds like we do, just not sure if he’s just moving out of this home).