Thanks for your help. Here are some closer photos so you can see what we are worried about. The house is definitely an older house from the 1920s and the roofer told us our old roof was done exceptionally well.
The type of vent isn’t something we see much out this way and we see some tiles curling up there. Do we need to be worried there?
Also I put up a better picture of the flashing. Should it be gapping in the front? I haven’t been able to get up there yet to see the back.
Then the skylight photo shows in the back corner where the flashing seems to jut above the light.
Last photo is from the front of the house where there is gapping in the flashing at the peak of the roof and the wall. Is that prone to water damage? Should that be flush with the wall?
Also is It normal that the trim on the house would be damaged and not repaired from a roofing job? Is that typical and expected?
Thanks again shedding some light here.