if it has wood shake, it will likely need all new OSB decking, but even with that and 2 layers of shingle removal, you would be at no more than $500 per square or around $9K in my market in KC....I don't know of any roofers in your area but sounds like you should definitely be able to get it done  right for WAY less than $15k...if you don't get any good roofer recommendations, try BBB, Angie's List or NARI ( National Association of the Remodeling Industry) for quality roofers and get a few bids....don't trust a "guesstimate" from another agent or anyone else who is not a roofer

The roof was in poor shape - edges of the shingles pulled up everywhere.  

Arched shingled roofs.

Make sure the attic is ventilated well, if your living space is that hot, what is all that heat doing to your shingles?

Part of the roof needs new shingles.

.- The only rehab required seems to be shingles on one and it is not urgent to my knowledge.- Taxes - $653/month- Insurance - $125/month- Property Management - $425- 10% for vacancy, 5% for maintenance.I appreciate any and all comments, thanks guys!!

I have a relative in Cheyenne and another in Sheridan (who was a contractor for many years) who are helping me get an idea of repair costs, which I round to the next highest $5000.All the repairs which are needed are listed below.I know Zillow and Trulia are not good sources - I only put them in to provide all the information I have.Repairs: New shingles for roof.

My contractor (at the time, don't hire that guy) ordered shingles in a different color.

Turns out my roofer screwed up, water was able to get under the shingles and ruined the kitchen ceiling. 

I have a loader to get the shingles up on the roof .