how well you've posed your question(s).. and I'm going to be checking on answers because this is a major home improvement project that is needed here too. I hope some knowledgable people respond this one..

Let the roofers damage the old stuff. And if we get a torrential downpour in the middle of the job, at least it's the old fascia/soffit getting wet. Then either the roofers replace it or another handyman does.

Certainteed architectural shingles actually come in a few different materials. How long each one lasts depends on what they made it out of. A typical asphalt shingle roof, properly installed, lasts about 15-20 years. They can make asphalt shingles that last longer. Other materials last even longer.

When they keep replying "lifetime", ask them what the lifetime of the shingle is - there is no "forever" roof. The longest lasting roofing materials are certain kinds of metal roofs, which last 100 years. So ask them how long in the future you can make them come out and give you a new roof for free.

As for pricing, your best control there is to get bids from at least 3 contractors. That will give you an idea if anyone is particularly overpriced.

WARNING: DO NOT AUTOMATICALLY TAKE THE LOWEST PRICE.

1) If one of them is dramatically lower than the others, that's probably a bad sign for the lowball. For example, two come in at $10k-ish and one comes in at $7k-ish (30% lower). He may be cutting corners, or will tear off the old shingles and find "problems" during the job that require more money until you're paying the same or more than the higher estimates. There are rare cases where someone is doing the work cheap for a good reason, such as being new to the area and thus needing a client history. If he doesn't have a good reason to be way under market price, run. If he says "I'm just better/faster/cheaper than those guys" run faster.

2) You're trying to ensure the costs are reasonable, not the cheapest possible. If you like everything about a particular contractor, but he's a little more expensive, you should go with him. You will be happier in the end.

and I would expect a total roof replacement to do the same.

The price seems about right for a job done correctly. Don't forget, it includes stripping an unknown layer of shingles along with any underlying structure that has rotted, down to and including any rafters with dry rot. Total roof replacement is a bigger deal than having somebody nail another layer of shingles on.

"Lifetime" isn't good enough. Find out what the warranty is. Also research the roofer's reputation. Roofing and driveway repair seem to be grifter magnets.

The house was built in 1987.

As for damaged rafters or any other dry rot, those costs per the contract would be additional. That is the scary part since it is unlimited.

I am researching reputations as much as I am able.

as was indicated above, replace the fascia/soffit after the roof and don't necessarily take the lowest bid.

Shop around, get recommendations from whoever you can locally, check out the companies online for reviews from others who have had work done in the past.

Talk to neighbors and friends about contractors they've hired and would recommend.

I need him to replace some rotted boards on the front porch anyway so he said he would look over the entire job. Since I have been using him for over ten years I trust him and he knows what I expect.

He is very familiar with the house and said he believes he can save me money.

Plus he doesn't speak down to me like the roofing salesman insisted on doing.

I am feeling much more relaxed now.

how much repair work it's hard to say. Plus, the architectural shingles add to the cost. We went with regular shingles cause I don't see the big deal about the others.

The first because they put more mass on the roof, the second because there aren't any slots cut in them.

Or more precisely, the short warranty has gone away.

I looked up CertainTeed's warranty on the shingles you're talking about. There are three warranty phases.

To the original purchaser:

Phase 1 is the "SureStart" warranty. For the first 10 years, CertainTeed assumes 100 percent of the cost of fixing your roof if their shingles fail. You can assume they're going to have someone up there going over your roof with a fine-tooth comb trying to get out of the warranty, but they wouldn't be an American corporation if they didn't.

Phase 2 is the prorated period. From year 10-and-a-day to year 40, they only pay for new shingles and they reduce the amount they will pay you by 1/600th per month.

Phase 3 is from year 40-and-a-day until the original purchaser dies, sells or whatever: 20 percent of the cost to replace the shingles.

If you sell your house within the first 10 years, the new owner receives warranty protection for 50 years.

Since very few people keep their homes long enough to run out of roof warranty anyway this is mostly a marketing thing. More important to you is the wind warranty: 110 mph, valid for 10 years.

New gutters are expensive.

although I like the GAF company better. CertainTeed has more options, but GAF seems to make a sturdier product