When contemplating hiring a contractor check with BBB and references and thier current project go see.

Upsides  / downsides vs hiring an external property manager?  

For instance contractor buyers will pay more for properties because they don't have to hire a general contractor vs an investor who does have to pay GC costs. 

They are always looking for employees and you would be an easy hire with your gaming back ground. 

If I can't be there during the day, should I hire a GC, meet subs myself or hire project manager to oversee subs?

If you're going to have multiple members, and need a very clear operating agreement and exit strategy, you should hire one (and we'd be happy to help). 

The tenant is provided the Home Warranty company 800 phone number at the lease signing.If I run the financial on this, It would cost $400 per SFH times 60 homes = $24K per year vs hiring a contractor for $600 - $800 a week on average. $700 times 52 weeks = $36,400.What are pros and cons?

I also have the ability and tools to do most work myself, although time constraints will dictate that I hire contractors.

Two pieces of advice, don't try to do it yourself (it is far to important and messing it up can't be undone) and hire a professional.

Mostly peeling paint issues and obviously anything that has to do with making the home not in a livable condition. you can hire a HUD inspector/consultant to come out and inspect the property for you and tell you everything.