If it is shingles, look for wear and curling and if there is more than a single layer of shingles.

When we do a roof that's usually house+garage+gutters with a heavy 35 year dimension shingle, ice and water shield, new valleys and flashing; you are up there.

The roof features architectural shingles, adding depth and texture to the overall aesthetic.

You may want to look into getting a rubber roof put on and those are more expensive than asphalt shingles.

In Chicago, both low-slope and pitched (with fiberglass or asphalt shingles) are both common types.

Don't look for computerized stuff till you understand the basics and don't buy any property until you know how to analyze the numbers and tell a deal from a dog. 

The roof I may do IF you could show that it is end of service life, but newer architectural shingles can last 30 years, so a 20 y/o roof doesn't necessarily need a replacement just because it is 'older'...actually the only one I might do because its easy and low cost is the caulking, but even that would just be a token gesture.

They can be very tricky and it's easy for them to cause damage to other shingles while trying to do repairs.

It's elevated so flood damage was only done to the garage, but my shingles and some siding blew off and caused major water damage to the interior of my home. 

Hello BP family,I'm in contract for a home built in 2021, upon the home inspection it was found that about 1/4 of the roof has these defected shingles that have a line/minimal crack through them.