That title is my cleverness for the week probably. I'm trying to decide WHEN to do a new roof on my house, and if I should do one on my garage. Below is an information dump - please help me figure out what to do.
The current roof is ~12-13 years old. It was a DIY job by a previous owner and based on the rest of the DIY stuff I've seen, he cut corners sometimes. Biggest issues appear to have been the cheaper version of flashing. I'm not convinced there's decking under the current roof though. It's an old house, and probably would originally have had cedar shake, which has been removed, so the unfinished attic has the original horizontal planks and I see what looks like black paper in the gaps. Shingles are in good condition, 1 layer. Traditional asphalt on most of the roof, there's also a utility room addition (12x15 ft) that has a rubber roof. There are 2 dormers, one on each side of the house.
These dormers have been a source of trouble. About 2 years ago I had the sides of the dormers reflashed (new siding on the dormers, etc), which seems to have solved those water leaks. One dormer is showing new water damage in the bathroom, the top and around the dormer has been patched several times, but the leak has reoccurred several times. It is active again, but seems slow. At this point, it's clear that the water is travelling/the problem is more systemic. I have attempted to get a bucket under it to catch the water, but it's not working - it's inside the dormer and I can't get anything in there.
There is also a brick chimney which intersects with both the rubber roof and the main roof. Chimney is lined, and I know that there's some issues with the brick. Don't know how bad, but I picked up a piece of brick from the backyard last fall and I've been told the flashing is interesting (you don't want your knowledgeable friend to laugh when you ask about the condition/method of flashing). Something's going on. No known leaks at either roof intersection, but it'll need something in addition to new flashing.
The rubber roof seems fine, I'm not aware of any condition issues but also have no idea what to look for. There's no leaks that I can tell.
The garage is detached, was last roofed the same time as the house. I added drip edges to the garage 2 years ago. There is 1 known leak in the garage, but I don't know if I need to care. It's just hitting the already cracked slab.
So, thoughts? Do I need to reroof this year? Can it wait?