I'm not a roofing pro, but hope I can shed insight anyway.
Previous owners put a second layer on the house, using 30-year shingles. After 15 - 18 years, they were shot. As we got bids to re-roof, every pro we talked to, along with several home-improvement newsgroups and magazines, all say that putting a second layer on will drastically shorten its life. As I looked at our roof, I believe them.
So we reroofed our house 6 weeks ago. My son (who had been involved with a half-dozen other reroofing projects over so many years) assured me we could do it ourselves, and I listened to him. MISTAKE!

The couple thousand I "saved" by doing ourselves would have been a wise investment, IMHO. Yeah, we got the shingle shovel and other tools we needed. But my son estimated he and I could remove the existing two layers in one 10-hour day. After 12 hours, we'd only gotten off about 1/3! It seems the house was originally built by a high school building trades class, and the kids apparently thought their grade depended on how many roofing nails they used

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Anyway, my suggestion is to hire it done, and specify a tear-off.