If overall the shape of your
shingles is good, then you should be looking for a leak such as I have asked about above.
Flashing will be easy to seal or replace. Even a damaged shingle can be replaced.
Roof problem
I have water leaking from gutters. Had a roofer look at it and he said the roof flashing that is on there doesn't come out far enough. He said I could just get some new flashing and install it.. Should I just remove the old flashing and install the new, or can I install the new over or under the old?
Is the water spilling over the gutters or is there a leak in the gutter? Is the flashing coming out from under the shingles as an extension into the gutters? Anyway, always take off the old and then install the new. It always works better for me if I have a good working surface.
Leaking awning
My awning is just under the lip of the roof above the front windows. The slope to the awning was built not to allow water to readily run away from the house; thus, water flows directly on the windows and into the house. I would like to know if there is some waterproof caulking that could be placed between the roof and the top of the awning. Is there a compound that expands into place and would be waterproof/weather resistant?
There are more types of caulking then you could shake a stick at... so that can make it harder not easier right?
Go to the hardware store knowing what the material is you will be sealing between... i.e. the awning and the roof. Ask or look yourself at the different caulking material. Most will not expand, but you can lay in several beads to build up an area. There is also a backing material you can insert in wide cracks so allow you to use less caulk and form a better seal.
The silicone sealants last longest, but if you are sealing to asphalt roof shingles, you will want roofing caulking...