After asking around at work and talking to neighbours, I called a few more wholesale roofing and siding suppliers in the city, and I was pleasantly surprised to learn they were significantly cheaper than Home Depot. Depending on your driveway and where your hydro lines run, most will also deliver the shingles to your roof. This is a HUGE help if you plan to do a roof on your own.
With the offer from my family to help, which included the assistance of a contractor (my uncle), it was a no-brainer to do it ourselves. Even after my neighbour commented it was worth the extra $1000 to pay someone else. In this case, it was over $2000 difference, and since I was maxing myself out on the supplies, it wasn't even an option.
I also took the advice from a coworker and rented a dumpster. This was a wise investment, because it saved us time and a significant amount of labour loading truckloads of shingles and taking them to the dump. The rental company delivered and will pick up the full dumpster and get rid of the waste. Easy-peasy! And, with my luck, we likely would've ended up with a nail in a tire also, so it was an excellent idea to keep all the old shingles in one place and off my lawn / driveway.
It was a long, LONG day, and it was definitely a little hard on the body standing on a roof all day. Luckily, it was not too hot, and the rain managed to hold out until we were finished. I even helped! I was up there, shovel in hand, popping out nails, ripping the old shingles off, and carrying piles across the roof to the dumpster. Amazing how your fear of falling subsides when three others are walking up and down a roof like it's no problem!
Here is the final budget for the new roof:
Shingles (30 Year from a wholesaler) - $1082 Plus $40 delivery
Dumpster - $241 (includes delivery, pickup, disposal fees and taxes) - Mine was 6 cu yards, this held about 50 bundles of shingles and we needed 48 for my roof. Perfect!
10' aluminum drip edge, 1 bundle of EaveGuard (both for added durability under ice and snow) and 1 bundle of tar paper - $101
Nails for nail gun - $200
Gift for my uncle for helping - $45
TOTAL COST FOR NEW ROOF - $1709 !
Love for my brother and dad - priceless!