New Roof

Before we closed on our house, our inspection revealed that we would need a new roof ASAP. The biggest problem that this posed for us was that we were planning on closing on our house at the end of November (we ended up closing on Dec 2nd). This meant that we would need the new roof put on before the snow fell for the season. This left us about a week to get it done. Luckily, Matt had spent a summer working construction before he went to college and he had made some pretty great connections at that job.

Our nasty old roof and broken vents that let raccoons into our attic:

If you're looking for a great roofer in the Southwest suburbs of Chicago, I would highly, highly recommend Miles Construction out of Lockport, IL. Miles' team came out the day after we closed (Mr. Miles himself came out to our house before we even closed and took measurements and surveyed the work).
They tore off the roof in two days and started putting the new roof on. We were delayed in finishing the project because we had some hail for about two days, but they covered the roof with tarps until they could get back up there and put the shingles on.
Since we were getting the roof done anyways, Matt and I decided to use that opportunity to add two skylights to the front of the house. We got the skylights and flashing kits from eBay for about half of what they would have cost at Home Depot. Miles' team started by cutting the holes for the skylights from inside the house.
They framed the holes out with wood.

And they finished the wood with flashing to make it watertight. I like this picture because you can also see the style of shingles we picked out.

My brother sweeping up some of the construction mess inside. We seriously would not have anything done on this house without the amazing help that we received from our families.

Finally, they installed the skylights. It makes such a huge difference in our front room