Thank you, everyone! I really appreciate all your input and I’m excited to be putting together a list of options. To answer some of your questions:
I live in the mountains, closer to Steamboat than to the Front Range, but I’m well aware that most of the opportunities for learning (and of course events and shows) are along the Front Range. Denver metro is closer than Fort Collins, but I can go to FC a back way with zero traffic, which has some benefits.
I just found out that one of my favorite instructors will be coming to my area for the summer, so if I do move my horse, it might not be until the fall. And then my boy would either stay through spring or simply be there year-round. (Flies drive him CRAZAY — behavioral changes and even hives — so mountain summers may be very useful unless I can get the fly issue conquered. I’m going to be testing the SmartPak supplements this year.)
As a side benefit, winter visits to the Front Range would alleviate some of my seasonal depression. Compared to where I live now, there are definite advantages to experiencing the (relative) warmth of the Front Range and a chance to regularly glimpse actual ground not covered by snow. The six months of permasnow blanketing the ground here this past winter was too damn long for me, but my S.O. is a native of the mountains and won’t relocate, so it is what it is! Fortunately, my S.O. is supportive of trying this horse-move.
Steamboat wouldn’t be warmer or less snowy, but it’s closer, and that’s handy.
Depending on lesson times and location, I would either commute on riding days (I’m aware of the usual traffic patterns along I-70 during ski season and in the metro area on weekdays), or rent a room/AirB&B it as needed, occasionally staying with friends. I know this setup sounds crazy to most people, considering the potential distances and time spent in the car, but I’m eager to learn and explore this sport and I have multiple reasons to try this out.
As I wrote in the OP, we will never make it to the upper levels due to my advancing age (and our talent constraints, I’m sure, sigh). I’m okay with our limitations, and they don’t stop me from wanting to absorb all I can anyway. I want to learn, progress, and have fun. Huge bonus if I can make friends along the way.
If I don’t try this, I’ll just keep wondering if I should. So: Have trailer, will travel. 