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Hey there @the-old-coach . First off yes, I do know the feeling. I feel disappointed and things don’t seem to be going right (or at least the way I’d like them to go 😉). It can be frustrating.
It sounds like you are doing what I do at this point – take a step back and re- assess.
As far as missing playing seasons, don’t beat yourself up. As you said, life happens. The past is the past and can’t be changed. We can learn from the past though. Looking back to reflect on possible alternatives may be helpful. Then get back in the horse!
Re barre chords – these are tough on my hands as well. I took the skills course “better barre chords” and it does contain some good guidance and techniques to at least understand the mechanics of making a good barre chord. From there I have found it takes consistent practice (surprise!) and time (surprise again!) to improve them.
I have to take my barre chord practice in small doses – using short intervals, playing something else for a bit and then coming back to another short interval. Also, I put a day or two in between barre chord work to give my hand a break and recover. Finally, I do hand and forearm stretches every day that help. There are quite a number of YT videos on the topic (search for guitar hand stretches).
One thing I have found that helps me improve my barre chord playing is angling the neck up at between a 30 to 45 degree angle. Don’t know if this will help in your case.
Sorry for rambling on a bit. Hope some of this helps. Hang in there!