I'll echo everyone's sentiments and say to try to give it a shot by talking more with them.

Does this strategy seem too intense for a first shot in the rental world?

A cricket stadium was recently shot down, but talks of a town center replacing the parking lot on the West Side of Campus are brewing. 

I never missed a single payment and they made $50,000 in interest off of me over the last year so instead of foreclosing on me recking my credit for the next 7 years and them being forced to sell a house for less than what I still owe, it seems like a great win-win option but I was shot down over and over because the appraisal was just too low.  

Chances are they still wont allow it but it's worth the shot. 

Consider twilight shots for that "wow" factor.Offer amenities that make your property special, like a fire pit by the lake, kayaks, or paddleboards.

It’s time to fly and create the prosperity I seek or crash and at least know I took my shot.  

He was attacked by pirates, both he and his dog were shot. 

The wax ring could be shot, allowing water (and possibly sewage) to leak out around the ring and soak into the floor.

I just shot you a direct message.