You can just click on my BP profile and go to my Everyday Home Repairs website where you will see the 3 videos stepping through "My Plans," "Progress!"

(note: I only monitored the progress of these roof repairs, never was involved in the paperwork or process through the insurance company)What do you think I should do; wait to get estimates from local roofing companies, or call insurance to file a claim first?

I haven't progressed to a registered letter, but will do so if I don't hear from him shortly. 

@Brad Seidel, I see two other bigger risks:The HOA fees shoot up and/or there's a large special assessment.

A relative of mine just bought a house there for three quarters of a million dollars and Butler County assesses it at $41K.This goes a very long way to explaining why the community of Cranberry Township exists.

I have been making steady progress towards purchasing my first investment property in Milwaukee, WI, just need to build up my $ reserves before I can pull the trigger. 

Therefore, I got into a property that was not perfect but it was in a good location and good enough for me, at the time, to start my journey into REI.I personally believe in the motto of "progress not perfection".

thanks for the mention @Chris Tabanico and I think your assessment is pretty spot on. 

@Louis Mitchell IV 3 months later, any progress?

You should only agree to pay per progress arrangement, and have a 3rd party to be your eyes on the ground.