Find a roofer who is accustomed to working with investors and you can get it closer to $200-220 per square.

You may think the roof needs $500 in "repairs", yet no roofer will put his name on a $500 fix, to a 25 year old roof that needs replacement in his eyes.

These are companies who do the full renovation, and may use other subs, such as roofers, to finish the whole project. 

The husband is a builder that spends every day on maintenance etc.He comes from a family with brothers and cousins who have been roofers, plumbers, carpenters, their entire lives and are available when he really needs them.

A good honest roofer can give you an idea of how much life is left in the garage roof. 

You, on the hand, probably don't know the cheapest roofer, GC, plumber, asbestos remover, etc, person in town who is also reliable.

For example, instead of paying $1,000 to the roofer who replaced shingles on your other rental, you gave him keys to you your vacation condo for a week ($1,500 worth).Kindly advise.Thanks!

I work part time as a roofer and I will continue until I have a solid client base.

-most property managers have good relationships with services that are used often, roofers, plumbers, handymen etc. they can help you get quotes quickly on work that needs to be done.

Many times I ordered pizza for all and had a beer for them....limit on the beer depending on many factors (not for roofers, LOL) and actually I know it kept some there who would take off at lunch and have 6 and may or may not return.