My neighbor had USAA and was finally able to get them to pay for a new roof three years after hail damage and two years after all of the surrounding houses had their roofs replaced.

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.

Roof, landscaping, HVAC etc.

Searching through the MLS listings, my eye is constantly diverted away from searching for profitable properties to admire a Second Empire Victorian with a beautiful Mansard roof, a stately Greek Revival, or the sleek lines of a Mid Century Modern.

This scenario is usually only the case with mobile homes attached to land.Long story short is that you should fix the holes in the floors, holes in the walls, holes in the roof, fix the electric and plumbing if broken.

It was leaking when we purchased the property, but our best estimate was the last reroof was in 2004 when the latest addition was completed.  

Cost per foot/etc.)New roof?

It needed everything; plumbing, electrical, HVAC, roof, windows, insulation, drywall, flooring, all new fixtures.I had to remove the entire second floor and rebuild it; 2 bedrooms and 1 bathroom.

You don't want a special assessment for new siding or roof soon after you purchase.Matt's calculations are incorrect because he's using the $450/mo as the debt service, when it actually includes HOA & insurance.

I would spend the money to have an engineer do a complete inspection and have them include the expected remaining life of all the major systems, roof, HVAC, etc. in their report.Another area to look closely at is the commercial leases.