When I test rode my first road bike and the salesman asked "how does that feel?" I had to answer "Not sure" since I was completely not used to the new body position. I didn't know if I was too stretched or too bunched up because I didn't know how it was supposed to feel.
You are likely going to be leaning over a lot more, needing to hold up your head at a different angle. This will require training some new muscles. It will take a while to get used to it and for it to really feel comfortable. I needed to trust the salespeople that the fit was basically right and could be dialed-in later.
It sounds like you talked about riding more upright and about head tube length. These pretty much go together: a longer head tube (the thing the stem fits into) generally places the handlebars higher. I say "generally" because there are other factors like stem angle and spacer rings that also affect handlebar height.
I ended up with a Specialized Sequoia. It's got a longer head tube, more upright position, and more "relaxed" geometry. Together, that all means that you don't need to lean over so far and "stand on your head" like you said (my handlebars and seat are at almost identical height).
I love my bike. You can get a "base" Sequoia for $770. The Trek Pilot is supposed to have similar geometry and riding position. I never got around to test riding one because I fell in love with the Sequoia.
BTW I've always ridden in MTB shoes, both in cages and clipless; I really like the idea of a shoe that you can walk in.



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