@Mike McCarthy hit the nail on the head.

Are we supposed to document every minor scratch on the floor and nail home in the wall? 

 Hey @Pope Lake , great detail in the post, we can appreciate that as most just say "help me buy real estate" which gives us no ground to stand on, so thank you.I think you really need to nail down your strategy.  

@Kenneth - Charlie nailed it earlier.

They will sometimes be willing to write out things already in poor repair and cover the things you really need to protect yourself. i.e sometime you don't need to insure a bad roof, but you do need liability for a rusty nail, etc. 

As I know of at least one guy that runs mixed crews and is more than willing to train anyone (they do some GC work, concrete polishing, and carpentry, though mostly sub out plumbing, electrical and HVAC), as long as they show up on time.

@Mindy JensenThe siding should not be nailed all the way in it needs to be able to expand and contract, check to see if the siding was nail to tight.

Tenant used nails to hang many photo frames in the wallsQuestion:1.

Even if you don't have handyman skills, much of renovating a property is grunt work like washing walls and floors, painting, cleaning windows, caulking, scrubbing grime off tubs and sinks, polishing faucets, and so forth.

Chris hit the nail on the head in regards to school counting towards employment history!