We are looking at getting a new roof next year as this is when finances will be available. This is the original roof that was put on in 1992. We had it checked in 2016 and the estimate was 2-3 more years

This past summer in Central MD, we have had record rain. Last week I went up in the attic and looked around and notices some wet spots and dark spots. I also went outside and took some pictures of the roof where the inside spots correspond to the roof.

First pic shows the inside attic vent pipe. Pic 2-4 show the the outside matching area of the vent pipe.

Not sure where the water is getting in

Pic 5 is in the attic and shows a dark spot. Pics 6 and 7 show matching area outside. I think the attic spot is to the left of the pipe but I can’t see how water is gaining entrty.

Last pic is a general pic of the roof.

Can it survive our winter or should I get some of it repaired to get through until next spring/summer?

 

Those dark spots are definite signs of water and pre-rot stage. Most likely it will last the winter but the wood will need to be replaced if you wait. If re-roofed now depending on how bad the water stains are, the wood might be saved. A patch work or repair might help.

If considering a new roof, consider a metal one. Cost more but will most likely out last your lifetime if you decide stay in this house.

 

It is common for the rubber gasket around roof vent pipes to crack with age. It looks like someone already did a goopy repair on one of yours. Here's a This Old House video.

 

Got one bad boot and one installed wrong.
One of these will fix the bad seal.
https://www.homedepot.com/p/Oatey-1-...E&gclsrc=aw.ds
The bad install will need a few shingles to fix it right.
The shingles should have been ran over the sides, not cut back so far, and someone did not cut the shingle back far enough at the top so it's not laying flat.
It' would take about an hour to fix all of this.

 

I had the same issue on my house, and it was due to deteriorated caulking that was sealing the gasket around the pipe. It looks like you definitely have some old dried out deteriorated caulk. Rather than replacing them, you can simply buy replacement ones from the hardware store and slide them over top as a temporary fix until you get a new roof. I did this 5 years ago and haven't had a leak since. Roof flashing vent collar: https://www.homedepot.com/p/Oatey-1-...E&gclsrc=aw.ds

Just realized Joe already sent the same link. This is also what I recommend