You have to actually "hit the pavement and knock on doors" as they say.

Doesn't make it so, anymore then saying blacktop is ugly.Fresh paved or sealed asphalt to a lot of people is a lot more attractive than washed out colorless gray concrete.

Not only will it be aesthetically awesome, I'm hoping it outlasts asphalt shingles by 3 fold.

The pavement and building retain heat and you can feel it getting cooler getting out of the downtown area.

No , not a problem , water hits hard surfaces , brick , concrete or asphalt .  

.$50k is easy if you pound the pavement, call expires, call FSBOs, do open houses, etc.

Is it asphalt or concrete?

Extent of rehab would be interior demo, new interior finishes, asphalt shingle roofing, vinyl siding and landscaping improvements.

Nobody ever gets to those high points without pounding the pavement and trudging through the monotony that you're going through right now.

Is it going to deteriorate the concrete slightly faster, possibly, but you are not looking at imminent failure from what I can see in the picture, and likely will not effect resale in the slightest.Beyond that, you can try to lift it, cut out the trouble spot and re-pour, asphalt over, or completely remove and repour.