Remember, clear communication is key to keeping a strong working relationship.

Goals: Keep building my portfolio.

Because in a year or two you can move out and keep the entire thing as rental with great financing. 

Those who are keeping the loan in-house often impose more restrictions and tighter terms (called "overlays") than those who don't.Do you have a model in place to figure out a purchase price? 

They are going to "see" every transaction and this keeps the IRS happy.    1.

You may find it’s just analytically better to keep the original property.

Tenant keeps a bank account and credit card on file with Obligo, and they authorize Obligo to withdraw money up to a certain dollar amount.

Basement installation doesn't make a lick of sense IMHO.Just keep the hot tub at the heated setting for winter months.

Bottom line is in my humble opinion is to just keep it simple. 

.- Hire a solid property manager who gets paid to keep tabs on the property for you.