I want to be dead before I have to do it again

Number eight on the list of summer goals (in no particular order) is to replace the roof. The existing roof is obviously failing with missing shingles, granule loss, and signs of slipping/sagging shingles. I tried to get someone to come do a quote on doing a temporary winter fix to stop the leak (where the shingles are missing) but I couldn't get anyone to actually get out to the house and do the quote before the snow started. After that I kind of gave up and figured I'd just try and fix whatever additional damage resulted. You'd think that 3+ layers of shingles would offer superior protection from the elements - not so.

Like I mentioned, it appears that the roof has more that three existing layers of roofing material; I'm pretty positive that the original roof is still up there. In addition to the poor weather protection the current roof provides, I think the combined weight of all the shingles has got to be a bad thing for the continued structural integrity of the house. Since we got an estimate on replacing the roof on the house we didn't buy, and saw a thrice faxed copy of an estimate done for this roof, I know that the cost to rip off, re-sheet, and re-shingle can run from $8000 to over $10,000. Yikes!

Since I come from a family with a "I could do that myself better and cheaper" aesthetic, my dad has convinced me that we could replace the roof ourselves. So now that summer has come, rather quickly I might add, I am rushing to organize everything. I mailed off my permit and check to the city so we're legal and all, I found the shingles I want, and hopefully everything will fall into place for the 4th of July weekend. After a little internet research I found that laminated shingles (also known as architectural shingles) can now come with a 50 warranty. Now that's my kind of a shingle. I never want to put on another roof and if I'm 80+ when this one fails, well we'll deal with it when the time comes. I'm looking at the TAMKO Heritage Vintage shingles in green. I still have to go to the lumber yard tomorrow morning to order them, and all those other things like underlayment, iceshield (required by the city), drip edge, and a ridge vent. I'll also need to get new decking, new flashing, and vent pipes but I'll get those when we're ready to get started. I know this won't be an inexpensive project but I hope to fall short of the $10,000 mark.