I'm under the assumption that a property being sold with a 30yr old roof in need of replacement would be valued (or even assessed) at a lower amount than the same exact property that just had a 30yr roof done?

I understand one way is utilizing depreciation to lower my active income's taxes, but when are people pulling out salaries to utilize in their non real estate life.  

Yes, I searched a few different municipalities in various states and all have various levels of accessibility (free online records, require written request, must visit office in person, etc)

One of the problems is that it is surrounded by a couple of lower income communities.  

The question is though what level of success do you want and do you think it's already time to celebrate?

I might suggest offering a lower rent than what they pay month to month as an enticement for going long term (and that could mean either offering a lower rent than what they pay now, or raise the rent if they want to pay month to month).All those little decisions you'll just have to feel out what works with your place and tenants.

I received 2 quotes for the roof replacement prior to and both quotes are lower than what I put the estimation at, I added about $2500 more after receiving their quotes.  

The level of interest dropped severely once people had to pay for it.  

I would suggest driving for dollars in the area as well as Popping into The Barn and asking the real estate developers who own that building and office on the lower level if they know of anything.

It also comes from increases in education spending at the local level.