Still at a point of:
- Do I need to replace it or can I wait - how to determine, who to hire for objective evaluation.
- If I do, I assume I should buy solar panels with it (this company does those also or I can get them elsewhere than the roofer). Buy with roof or wait?
- Selecting type/brand for roofing, contractor, if I do it.
1. I would need to see very detailed pictures to even hazard a guess, and it would still be a guess without me putting eyeballs on it, as to whether you need a new roof or not. There are some pretty obvious signs that I might be able to see but going off of a non-professionals description has generally led me wrong. No offense. You are definitely in the age range of needing a new roof, so if you don't need one this year you should definitely be budgeting for one soon.
2. You can always have your roofers make your roof "solar ready". They install the solar mounts and make them watertight and at a later time of your choosing you can pick a solar installer to come install panels. This is a bit complicated due to local wind codes and such but it is possible. It would be better if you had both contractors working on the same page. I would NEVER trust a pure solar installed to penetrate my roof but this is simply from anecdotal evidence I have gained in south Louisiana. Your guys may be great at sealing roof penetrations, our guys think a dab of roofing cement or low-grade caulking will last a few decades. I have made quite a bit of money fixing their fuckups.
3. Brand of roofing is really up to the contractor you pick. They all have their preference because of backend kickbacks, it's just the way the system works. The big 3 are all relatively equal in quality and offer the exact same warranties. Keep in mind that the standard warranty that you get with any shingle roof is barely worth the paper it is written on. There are real warranties offered but in your climate I wouldn't personally expend the extra money for it as it requires more expensive underlayments and the warranty itself costs $1,000ish. As I said in a previous post, you will not recoup the money from a "cool shingle" versus a standard light colored shingle over the lifetime of the roof. If you still want to go with it then by all means, it's your money my friend but I am sure that it would be better spent in insulating your attic.
Edit: GAF Timberwood shingles are what I use most of the time, they are a good product. Certainteed and Ownes Corning have similar products all of which I am certified to install but I don't generally use unless forced by contract, I can say that they are pretty much equal in quality. Like I said it's all about the backend deals or what your supplier stocks.
I just personally wouldn't go with the cool roof option, especially if you can live with a lighter colored shingle.