It will make it easier for him to keep track of project with you. 

If they don't hang up or don't say no, you need to keep asking questions and qualify the property for condition and the seller for motivation.

Or do people generally keep their rentals in the same location so they are easier to manage?

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? 

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.