@Tucker Mason in our opinion, it depends on the Property Class/Tenant.Class A: most people can DIY manage and learn what they need to know on the fly.Class B: A bit harder, takes more time and there's more risk with maintenance and tenants.Class C: should only be attempted by EXPERIENCED landlords!

With inflation normalizing, the Fed is simply returning rates to a neutral level and they are guessing at the pace of cuts to get there (just like they guessed (wrongly) when keeping rates too low).

If it matters to any degree to retain this tenant, if listing for new tenant is a pain, I'd simply call this guy up, I'd be upfront and ask him about all this.

I simply thought putting it out there in the Forum might keep someone from unknowingly buying something that might leave you out to dry.

Ask the lender first before attempting to use a co-signer. 

If the house value goes down, the tenant has the option to simply not purchase and you would keep their option money.

.  --- and... these issues become issues for the other Tenant and then turns you into the constant 'utility police' because you constantly have to monitor # of occupants... eww. 50/50 is simple and simply understood and 100% while vacant is also simply understood.

I think you need to start by figuring out what you’re near term goals are - are you wanting to generate enough cash flow to offset W2 income, are you simply wanting to supplement your retirement, are you looking for significant tax advantages etc.

Then, upon resale, does this private lender simply inform the title company of the payoff?

So, you can't simply trust them to handle things on your behalf and often communication is challenging especially if they choose to make it that way.