My fiance is a big podcast buff.

The owner isn’t necessarily responsible and the driver should file a claim with their insurance but sometimes it makes sense just to pay someone to buff out the scratches 

I'll take your advice though and see what I can find out, thank you for your time, and the gentle kick in the butt. 

Newbie here please be gentle.

Are there ways to gently convince the lender this property is more residential than it really is?

You can let them know in a gentle and non-alarming way.

I would try as gently as possible to walk the manager through the missing funds and try to reconcile those, then part ways as soon as possible.I would also HIGHLY recommend changing the way you operate with regards to taxes and insurance payments. 

I try to gently let tenants know that each fall/winter, in an really old graystone, there are probably going to be some occasional incursions.

I would be gentle at first and remind him how long it has taken and Your willing to be easier to communicate with and make quicker decisions!

Sometimes you just need a gentle nudge to push you in the right direction.