And for the older buildings, there is a citywide program that mandates repairs of any eyesores (eg, my old roof must be replaced by June). 

, rehabbed them, and got everything stolen from under their roofs (including the copper wire in the walls), right before staging. 

The roof, floors, and appliances have been completely redone.

Well guess what it wasn't with several vacancies popping up, with some major repairs needed, a roof that was hit by a storm and some other plumbing issues, it pulled me tighter than I needed. 

Stuff on the MLS usually flies off the market if it's aggressively priced, and stuff that doesn't is usually pretty hairy (e.g. illegal apartments, city violations, leaking oil tanks, whatever else).

(Roof, windows, doors, HVAC)- large fenced in backyard - 2 car driveway in a location where driveway is not common- Overall, interior is up to date and property is in a good condition and area.How would one should approach this to make it work for both parties?

There's a difference between reading and doing.Besides, a book might estimate this costs to repair a roof, but the author can be basing their numbers off a different area and a different market from years ago.

I've seen comps that were blatantly incorrect, claims of new roofs/furnace/etc that were not true, etc. 

One thing a good inspector will have is moisture detector, and temperature sensing equipment, that could tell you if something is leaking somewhere. 

My wife does a video walk through every six months-long term tenants annually-she looks under sinks, checks alarms, looks for leaks etc.