I think there seems to be a general misunderstanding regarding exactly what my hopes and dreams are

I really am only looking for a solution that will allow me to communicate with club members on trail runs (that meets the clubs requirements). Maybe a handheld won't work for that, I don't know. Thats why I am here looking for real world feedback. I have no interest in talking to long haul truckers about lot lizards or whatever else it is people do with radios when they are not in a group on the trail.
I hear you man, your goals are clear. I understand what you're after. I get there is a club requirement and I understand not wanting to spend much time or money on a system that'll be rarely used. I really do, and by all means get what fits your goals, I am just sharing my real world experience... no harm meant. However, after 20+ years of trail time, I have learned lessons the hard way. I am only trying to help. To me trail coms are a safety item, not merely a convenience for conversations.
That said, I have YET to see a handheld CB without an external antenna transmit much further than yelling distance. I am not kidding, not exaggerating. I understand the club "requirement" and a handheld CB would meet that requirement/goal, but you won't be heard or "in the loop" of conversation on a trail ride... for new folks it becomes a source of frustration. For folks who can communicate and chat the one or two rigs without radios or subpar radios slow the group down. Everyone becomes frustrated. So on one hand you meet the club requirement (that's great) but on the other hand I personally think you'll be disappointed with the actual ability to communicate on the trail. If you're looking to come play on a trail run, come on out. I doubt anyone is going to DQ you for not having a radio on your first run. Maybe borrow a CB handheld and see how it goes? I carry a spare HAM to loan out to others for better trail coms, you're welcome to borrow mine to give it a test drive.
I remember a year ago Darren, Bryan and I went wheeling all around Little Bear in the Gallatin Gateway, at times I could SEE Darren (who was using a handheld CB) at a true 100 yard line of sight distance and couldn't hear what he was saying. We'd have to stop, get out of the rigs, talk through next steps etc. YMMV. I am not talking about chewing the rag with truckers 5 miles away I am talking about trying to see if everyone in sight wants to stop for lunch.
By all means, buy what fits your need... I haven't seen a vehicle inspection yet for a club ride. Radio's are for trail communication, all I am saying is the handheld CB's will meet the "requirement" but fall short of the goal of being able to communicate on the trail. Maybe they've improved, maybe they're as good as the family radio's (walkie talkie's) have become but that hasn't been my experience.
The advent of the inexpensive (Bofang and similar) HAM radios has really opened up good options for a handheld solution that works. The radio's can be had for under $50 and the only hangup is passing the exam to get your license. I haven't met someone who couldn't pass the exam with a little studying. The leap in clarity and distance from CB to HAM is like the jump from a rotary phone to an iPhone 11. I would imagine a handheld CB and an inexpensive HAM are about the same price these days.