It's not crazy if you want it bad. At some point, you have to deal with the weather, so you could make the change of temp/dp part of the experiment.
So much of your history resonates with me. I had a stylist for 22 years, and though she often did stuff I wanted that she thought I might not like (and she was ALWAYS almost right, like when I went really short or when I didn't let her do this or that, that after 10 years I just said, "Do whatever you want, I trust you"). She came to know me better than I did, since I'd want to chop my hair off come May/June cause it got so hot, but she'd remind me how I always regretted getting it chopped. (True.) Or when I was afraid to grow out my layers, she kept saying it would work, and she was right (I ended up with some of the prettiest hair I ever had blown-dried when I let the layers grow much longer).
But if what you really want is to try a change, then take the risk. If you realize it was a mistake, you can always go back to your more reliable cutter or just adjust instructions to whomever does it. Hair does grow back.
Now, before you do that, however, I suggest you do this with your regular hairdresser--tell her exactly what you just told us and have her do your hair USING YOUR DRYING TECHNIQUES, not hers, so she knows what you are dealing with day to day and what she needs to adjust cutwise to give you results you want (if possible, not all our desires for our hair ARE possible).
I only went CG five months ago, so I only got two hair trims with my stylist of 22 years before she retired. But both times, I took my products, took my microfiber/floursack towels, and asked her to diffuse with a bowl. Once, I had her supersoak for clumps.
If you show your stylist what you do at home, she can see how your hair turns out using YOUR methods, and will understand what the base cut needs ot be to give you a better result.
Just be as open with her and clear with her as you ahve been with us. And take a pic of what you want your sides to ultimately look like (the fullness you want). Visuals always help. In the past, when I had heat-styled hairdos, I would draw a pic of the general shape I wanted for my stylist. I can't draw worth a poop, but I'd do the shape of my face using a mirror, then just swoosh in waves, curls, straight parts, bangs in the general look I wanted. That way, I didn't have to use words or hand-gestures. I could show her the drawing and then she'd tell me if it was possible given my hair densitiy/traits.
I was almost always happy with the results in 22 years through bobs, waif cuts, heavy layers, light layers, long and medium curlies, straightened, etc.
Sometimes, our stylists just need a clearer vision and image from us of our ideals...
Granted, this would be hard for me to do with someone new. But with someone who's known me and my head of hair for XX years, that sort of openness and expectation is no unwarranted.
Note: If you air dry at home, this is not feasible in a salon, so that's something I just realized. But you can sort of approximate air-drying with gentle diffusing. If you plop, show her how you do it, etc.