I've done shingle roofs, metal roofs, and rubber roofs. The problem free roofs are the metal roofs. Why? People have a strange desire to get onto a rubber roof, and they do not realize the damage they are causing. 100% of the rubber roofs, had an injury from someone being on the roof. (high heals!, sitting on a chair to watch fireworks, etc). Shingle roofs? Shingle heat and fall out, or they get damaged, etc. (homeowners in the north have to shovel snow off shingle roofs). The metal roofs with a nice pitch shed snow fast. My lastest love...is a cold roof, where there might be two roof decks , and the insulation in the attic space can be packed to the gills. Imagine, But, for a mobile home, it's a metal roof elevated slightly above the insulation, with spaced out 2x4's (or such) provide a 1.5 inch air flow. Special framing at the ends(with metal screens), allow air to flow under the deck and water barrier and over the ridgid insulation. Works great in cold areas of the country.. Unnecessary in warm ares of the country.

Did they place a water and ice shield barrier on the edge of the roof to three feet past the wall line? Your roof is not similar, only the material is. Original roof was solid from eave to ridge so any ice formed would just keep backing up the roof without penetrating. New roof is pieces which allow the ice to form and move underneath and then leak in the house.

Mmm, I had my chimney reflashed this year and it was about 200 dollars (that included sealing and fixing a couple bricks) it has a warranty for five years I think. anyways, won't the new chimney have flashing? Then it will fail in about 3-5 years and you will have to get new flashing again also, regardless if it is new or an old chimney. So Eventually I think that it will look ugly, like the older chimney. also you have an old house and old house owners know it isn't as easy as you think (nor as cheap) if you tear down the top of the chimney I bet you will find other things that need to be repaired and the cost and time will increase! If it were me I would go with just the flashing repair. We had tar all over the chimney also so the repair was done with some sort of epoxy or something. It looks black but isn't tar. Anyways, the chimney looks SO much better now. I think they cleaned up the tar a little while they were up there. Because of the degradation of the chimney bricks, which were then tared over, it would be difficult to put the metal flashing on our chimney. Also the bricks are very rough. Our house is over 150 yrs old also. Our chimney is not used anymore though. We use the front chimney and we have a liner in that.

Through the roof vents go under the shingles at the top and over the shingles at the bottem. Period. No glue, caulking or cement is needed. If your code calls for larger vents you can cut the pipe in the attic and add a larger section to go thru the roof.