You can get top dollar likely, but it still needs to be reasonable and comparable. if it’s a declining town with not many attractions or amenities, then it’s likely there’s no rentals available because nobody wants to live there. mot sounds like you may be describing more situation #1, in which case it’s a ripe opportunity if you can get a deal on a property

Does the current lease have language describing how the lease renewal executes, determining new rent rates, escalations? 

Nobody who knows me would EVER describe me as a "shinking violet".

Given what you described I don't like it.

Based on the way you describe your business if you keep your contract management in order and maintain insurance certs from all vendors listing yourself and the owner (if you are providing exceptional service to your clients) as additinoal insured, you should greatly reduce trhe risk of your coverage being called upon.

Congratulations on your first successful project as a DEVELOPER.Put together a nice marketing package that describes the opportunity and sell it.

Describe the fees.Anything in the agreement about selling the property?

My lender seems a little iffyy, I'm not sure if how I describe my intended use of the property will influence if they give me a loan. 

Definitely a less stressful way to do it the way you're describing, but I would say that 0 down time is a pretty ordinary procedure / SOP, unless a unit is getting significant renovations.

The basic math they used to describe "replacing" your income was a bit shocking.