It also has slate shingles that I have maintained yearly, and I know if I get the box gutters re-lined they will be good for several years to come.

Because the HUDhomestore process is so computerized I bid on most every home in a desirable neighborhood open to investor bids.  

Missing shingles, messed up flashing, etc...It could also be a leaking (inside the wall) water pipe, or leaking drain pipe, failed toilet wax ring, or bathtub drain pipes leaking.You might want to budget for a scrape and paint  too.

Asphalt shingle roofs will curl, tabs will break.

The only problem I've heard of with replacing a roof in the winter, is the temperatures being too cold for asphalt shingles to seal properly. 

At this point I consider myself a ‘jack of all trades’ I can frame out a wall, hang and finish drywall, rip up a floor, repair the subfloor, put down new flooring, basic electrical work like swapping out light fixtures and wiring a run of outlets, strip a roof and lay down new shingles or a metal roof, install a window or new door, hang kitchen cabinets, tile and grout a backsplash, very basic plumbing work like swapping out a tub or sink, I can build outdoor structures like decks, ramps, etc.

I have a small project to cover up holes or replace clay shingles and most likely replace a flat roof.

I have used them in the area several times - though not in Pittsburgh proper just in the suburbs.If there only a couple shingles to repair I will have a handyman do it usually because I am getting several things done at once, so just pay for a half day or full day of labor and provide the supplies.

Pitched asphalt shingle?

It was on roof shingles, insulation and even in appliances!