We bit the bullet and got our roof done this April. Ben wanted to do it himself, but without the proper equipment and time it just wasn't worth it(never mind the fact that I'd rather pay someone else to climb our roof than worry for more than a week about my husband way up there). We got a great guy from London who works by himself so it was way cheaper than a crew. Katie took to him immediately and still talks about Heeearold up on da roof! Harold was a little short on time so Ben actually took a few days vacation and worked with him(getting a bunch of $$ knocked off the price).
Harold was going to a job up north for a few weeks and left his roof jacks up as he didn't need them. They were in the perfect spot for Ben to finish up the work on the dormer and chimney. So in the last couple weeks ago he repointed the chimney, trimmed the windows, hung the eavestrough, sided and painted the dormer.
We closed it off the spring after we bought the place and it looked like this (more or less, but without the middle addition) until last fall when Ben put up some energy board instead of the Tyvek that had blown off.
Finally! It's not ugly anymore! Ben just needs an elbow piece of downspout to connect into the eavestrough.