Most importantly, outside of a weekly meeting to discuss the property and any current issues they run it seamlessly without the need of my intervention.Second, have a good CPA who knows the area, specializes in real estate and who you can B.S with about real estate during phone calls or meetings. 

Then either I will make 2 phone calls and have an offer or give them an offer.

Not to sound like a broken record, but I echo the sentiments of everyone above. 

The roof company's phone number is disconnected and won't return any of my emails.

if its not damaged or broken i would paint and leave you can always siding maybe check Habitat

Ive contacted them by phone and email multiple times on both issues.

Do a little reading and then get on the phone with a few providers.There is a lot to learn, including a variety of plan service types (custodian vs checkbook for example).  

There are ways around it, but a phone call can save a lot of time, money, and effort.

He was always quick to answer the phone and work with me.

Then, look for distressed properties - ex. poor landscaping/tall grass, doors off hinges, broken screens and windows, etc.