I'd call a few roofers in the area off of Craigslist and ask them, in general, what they'd charge per square for a basic, asphalt shingle roof.

The storm blew off a bunch of shingles.  

But I had some damage , shingles , about a square and a half blew off 1 of my rentals , I will be using insurance on this one , its not minor .  

I vote stay in the PM role that you love and find another part time job or side hustle to add to your down payment fund.Can you get your own pest spray and tools and hang your shingle as an independent mosquito sprayer on off days, nights and weekends?

Just talk to a CPA about it or use a computerized tax program that will ask about the hardship.

Does anyone know how expensive cypress or cedar shingles are?

Mean while all of the shingles are buckled.

READ all of the through a few times BEFORE you visit a CPA.I always kept a "working copy" of the forms for each property, when I computerized in '95 I made it an Excel file and that worked fine for me.

Im thinking it will be in the 7k range since its a mansard (barn) style roof.The other problem is the asbestos shingles... havent gotten contractor quotes back yet.

Shingle mfg. has the same.