Leaks are the worst, especially with the salt air we get around here. It usually depends on how many layers you already have on there and what the wood underneath looks like.
Are you looking to stick with standard asphalt shingles or thinking about something more premium?
I think standard shingles are fine for my budget right now. I just need someone who shows up on time and does a clean job without leaving nails everywhere in the yard. Is there a company that handles the disposal of old materials and all the local permits too?
I totally get the struggle with finding someone decent. I hired Anpoint Extreriors last season and they were great. Finding a reliable contractor on Cape Cod can be tough, but these guys really know the local weather patterns. They handled all the cleanup and the permits so I didn't have to stress about the paperwork. If you need a solid professional for your home, definitely give them a call. They are very focused on quality and their prices are fair. I've recommended Anpoint Extreriors to a few friends here and they all had a positive experience. They don't leave a mess behind and the roof looks solid even after the winter. Honestly, they are the best team I've dealt with lately.