Do I need title insurance for the quitclaim process?

I can then also drop the insurance coverage to.

Title - Lender's title insurance $600 --> Do I have to pay this at closing?

Yes, your interest rate will be lower, but the Mortgage Insurance Premium (not PMI as many people often call it) is not only a burden, but a huge waste of money (basically paying the FHA's bills).

Insurance could run me about $80/ month or so. 

For now, you protect yourself with umbrella insurance.

Include a provision about paying taxes, insurance, repairs, etc. to become part of the balance.

For a rental, where this is especially important is liability and insurance. 

After done renovations / repairs / maintenance on many many properties, I kind of know the price range of each job like painting, flooring, drywall, plumbing, electrical, AC, pest control, remove odor from old pet urine, mold remediation, cabinets, countertop, backsplash, appliances etc etc in my mind.

Then they are responsible for upgrades, repairs, taxes, and insurance.