Does it need a new roof? 

At least with commercial (5+ units) you have shared roofs, can market a little easier (create a "wait list"), less exterior maintenance per unit, etc.

Purchased the house for $215,000 and invested about $25,000 for a new roof and other repairs and now it is valued at around $315,000.  

Have owned it for 6 years and remodeled 5 of the units, new roof, full occupancy, in nice area - but just getting tired of being a landlord as my kids get older and require more attention.

It was an area hit harder by the recession, home prices are still much more reasonable, and development in the area is through the roof.

While you are getting that piece of the roof repaired make sure nothing is loose and ready to fall and move on with your life.I would say to call your insurance to be certain you are okay in their minds, then rest easy knowing you are not at fault for problems other people have that are not caused by you.

Due to the lengthy process, steep learning curve, limited finances, and our desire to take action now, we are also driving for dollars.We live near the border between two towns, ours (Danbury CT) has a population of 84,000, the other (New Fairfield CT) 14,000.

Look at "life expectancy" of capex areas like roof, HVAC, etc.

It has a brand new roof which is $25k alone!  

I ripped engineered wood up with a roofing scraper and hit the glue with the razor.