loss of grit
broken or partially missing shingles
bent, lifted, or curled edges
shingle edges don't look like they have "square" corners any more
look for places that have high water flow will be in worst shape.
when walking on it you feed 'soft' or bouncy spots that are not the same as other parts of the roof
if you can lift the bottom edges of shingles up from the ones they are supposed to be glued to - BAD!
When you have water dripping from your ceiling you definitely know its too late
you may actually have drips, it doesn't mean that you are going to see it. sometimes it can run down insides of walls, or make your attic insulation soggy and mouldy. you need to also inspect the inside of your attic to see that there is no water damage on the wood on the inside of the roof.
Also 2 layers of shingles is the wrong way to have done it. it does not offer any better protection than a single layer, and is very heavy and hard on your roof. the guy who did it last was likely lazy
Really if your shingles are near the end of their life, all it takes is one big storm to lift a few that aren't sticking down well and you have a new water feature in your house which may end up costing more than the shingles