If you really want to find off market deals, you will be spending a lot of time pounding the pavement knocking on doors.  

hey everyone...i own a small business in decorative concrete and pavement marking....

Also, how long does the typical asphalt shingles roof last?

, roofing (asphalt? 

I recently had one give me a quote to replace asphalt shingles on a 1300 sf house, labor only it was 2,500 plus repairs plus materials about 2,000 so that brought costs up by 4,500; the guy called again wanted to do it at 2,000 plus repairs plus materials, I said "blah, told you that you only get one chance", did it in-house, it'll be done by Wednesday; 2 guys 1 day for repairs, 2 guys 3 days for replacement.

-asphalt company: reseal an asphalt driveway (most companies right now in the area only want to do a new driveway job!

Beat the pavement and find off-market deals?

In total, it looks like I need around 1700 square feet of what's currently a lawn to be converted into an asphalt driveway. 

In the original plans for the fix, the roof wasn't calculated but have already been able to save some cost in other areas and now the contractor asking if we want to have the roof redone as siding and gutters get redone because its asphalt shingles (believe that what type), essentially just really ugly.

Now those numbers mean NOTHING if your used inventory is 70 year old, asphalt shingled, asbestos insulated and lead painted properties in Hurricane, tornado or snowstorm regions.