Chris,There's nothing like experience when hiring a contractor.  

West coast we are still able to get em done in 30 days start to finish but boy I have a hard time having that happen in other states.. especially attorney driven closing states were the buyer and seller each hire their own attorney.. boy who ever though that one up.. the amount of back and forth between the attornies and mistakes and delays just cracks me up. compared to our title company clsoings everyone using one escrow officer to handle the transaction.

People and Capital virtually unlimited supply, TIME, is your most valuable resource.

I'm planning to hire a PM company, but I'm looking to have very tight control around who they bring in as tenants.

You can avoid probate with a "living" trust and still get stepped up basis, but remember attorneys don't know taxes so hire a good tax professional.  

Break the task apart and hire the inspection.

If I am planning to do some of the work myself and hire subs for the remainder, how to I present an acceptable rehab proposal to the lender?

It appears that the prohibitions' main purpose is to ensure that virtually all commissions are kept in Kentucky.

I plan to hire out the plumbing and electrical and do the painting, tiling and flooring myself.  

You're sending your drawings and tech requirements to a manufacturer in China, they make a house for you, ship it to your location, you hire a crew to assemble that house in your place.