You can always babysit them on some easy or moderate jobs to judge their skill and value.Took me at least 4 tries to find an electrician that was reasonably priced and knew what he was doing. it took trial, error, issues and money to get through the first three, but now I have someone I can trust. 

Deal doesn’t have enough meat on the bone 

It's often referred to as accessory living space (without cooking facilities) or an accessory dwelling unit (if it has a full kitchen).Unfortunately, there are a lot of contractors that will just take your money and build it without permits, leaving you with an unpermitted and illegal addition that you might have to remove later on. 

The “ deals” on the MLS have been picked through for sure but surprisingly there are still a few left with some meat on the bone.

buyer had an agent and an Attorney  seller ( me ) has and agent and my attorney.. it leads to some really disjointed confusing escrows to many cooks in the kitchen.in title company escrow company states your SEnior escrow officer is your attorney and they handle both buyer and seller.

Even though I've listened to the podcasts and read a few books, I believe a mentor would be ideal for me at this stage.

Rents could probably be raised but my tenants are on the struggle bus and they pay me monthly and don't bother me at all except maybe one problem per year so I haven't raised them. 

Let's look at it this way, say your a Veterinarian by profession and instead of a rental business you purchased a restaurant, would you be the "Chef" and cook everything?

I know it sucks to do that, but in Cook County it's fairly common.

It's difficult to acquire a  property with enough meat on the bone to make it worth while.