These are good questions, but keep in mind that a month of obsessive research is still the absolute tip of the iceberg.

My number 1 tip would be to go off market and find owner that wants to sell at a discount / prefers speed and convenience. 

Welcome to the community and be ready for a huge amount of information at your finger tips.

And I may get multiple bids for the same work, like multiple paint bids, multiple roof bids, multiple flooring bids, etc.

Adding paint and replacing flooring is not going to add much value in the typical case.  

Until he wasn't.Sometimes people change due to pressures we don't see, and sometimes people are just like m&ms . . . dark on the inside with pretty painted shells. 

On the advice of the fireplace guy who did our last cleaning/inspection, we sanded down the brick inside and painted it with the high heat black paint, and it states in the lease that they may use a fireplace-style candelabra if they'd like, but any other use will trigger all the rules in the Fireplace Addendum.   

Does anyone have any other tips and tricks for helping out the appraisal process so I can get the best out of the situation. also what what other things can I put in the folder to give him or what you've done in the past?

The tenant fails to pay their last month's rent and leaves the place needing new flooring and paint.

Property was sitting on market and needed light updates (roof, flooring, paint) but was in a great area that allows STRs giving me multiple options when deciding on rental strategy How did you find this deal and how did you negotiate it?