Yeah in that case, you’d probably be better off just picking up some decent GMRS handhelds. Spend a little more on some antenna upgrades, and you should have no issues. If you really want to stay on the right side of the law, you can have everyone in your group (who isn’t related to you) throw $35 at the FCC for some GMRS licenses. But, depending on terrain, you should be able to stay in reasonable contact with everyone with 5W if you’re within a mile or two.
I'm pretty sure you can find the same radio hardware platform but FCC certified for GMRS (or so the label says anyway). Maybe they added filtering to get it to pass? That means a $35 GMRS radio with USB-C charging, swappable antennas, and higher transmit power.
He's already seen Meshtastic, which is something I definitely want to play with for his exact use-case: coordinating with friends while skiing.