I received a quote from Mark DeLaquil at Eon Roofing and Window. www.eonroofing.com, He was willing to talk me through the repair I needed rather than charge me a couple hundred bucks for a five minute job.

As @Mark Miles mentioned, Option B will have a lot of hidden costs and likely hidden time-consuming repairs.

Ballast repair ($150) and a tech driving from store to store to replace covers. 

I’ve painted oil Derricks, built roads, built houses, remodeled houses, commercial painting, custom showers, foundation repair, truss repair, Roofing, excavation, it’s all a good time to me.

All we would like to do before repairing the ceiling is to get his confirmation that he no longer experiences any leaking.

I have also used proceeds of a HELOC to fix up and repair some properties too

The repair was a big hit for me, and I am now tight on cash, as I just literally moved and my wife and I are expecting our first baby so I am doing what I can here. 

I am trying to calculate how much to set aside for CapEx and repairs.

I can't say whether or not hiring a property manager would be better for you - not sure where you live and if you have the ability to find maintenance/repair people in OK easily or not. 

We are self financing all of the repairs and have completed 2 units after 8 months.