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.