Hey there Socks,
Glad you checked in: so hold the phone right there, sir, just pause and step away from that luthier for a moment!
1. I have zero idea about his skills, but anyone who recommends a bridge be shaved on a Taylor does not know about Taylors. So even if --if-- he is genuinely good, I'd absolutely not take it to this guy ...no way for me, period! Taylors have a bolt-on neck. And even with the glued fingerboard extension, a neck reset to achieve proper string geometry --and thus break angle-- is what you need for your classic, and it is not a "bad" job for someone who genuinely knows his stuff. You need someone who has done this before, a skilled tech who knows not only proper glue work, but who also knows these pre-NT Taylors.
By the way, are you certain he meant shave the "bridge" and not "saddle" ...this is a big difference and a huge deal here. Nevertheless, it sounds like a neck reset may give you that superb playability that is so common with current Taylors. But I don't have eyes on it, so take it to a guy who knows these pre-NT guitars.
2. A complete refret is not unheard of in a well-played guit. I have an 08 that I had refretted recently because it is my go-to guit for so much; it is not a big deal at all IF you have a genuinely good tech to do it. That said, since you have no divots and the frets are low, it sounds more like a personal choice for you: if you're ok with how it plays now, keep the frets. Yes, get a good level, crown, polish and it's like a good tune up for your fretboard; you'll like the feel and playability if you like how it is right now. But if your frets are really low from wear, don't be scared off by the prospect of a refret as a quality job can breathe new life in a guitar you already love. Moreover, you can choose whatever fret size you like at this juncture. Consider, too, Jescar wire which is harder than nickel silver (and not as hard as stainless steel), and you'll never have to refret it again, that means never. It costs a bit more than nickel silver but worth every penny, IMO. Again, these are options more than mandates so don't think that you need to do a refret by any means.
3. A new nut is common with a guitar played often. I had a nut replaced on an LP that is my go-to guit ...no drama involved. If you're considering a level/crown or a refret this is an excellent time for a new nut.
Same rule applies for whatever work you choose to have done: make sure this is a genuinely skilled tech. Ask to see his other fret work and he should be forthcoming. No balking. No resting on any laurels. Moreover, he should be accommodating to you and your specific playing style; any hint of being dismissive since he "knows best" is a "thank you for your time" moment and turn and go! Seriously, walk away. Truly good techs work with the player and his personal playing style as there is no such thing as his "expertise" that determines what is right. The genuine craftsmen know this and will work with you to achieve what you desire.
Hope that gives you some food for thought. Glad you've got a guitar you love this much ....kudos to you for keeping the gems in life!
Edward