@ Jason: “Once was when the ground was dry, rocky dirt that wouldn’t hold a stake and the other was in a violent thunderstorm in Sequoia NP.”
Yes, those would be instances where the “free standing set up” would be beneficial.
The pole jacks from MLD or others might work perfectly fine. If the pole jack starts to separate from the pole, you could always use a bit of first aid tape or duct tape on the outside to adhere the two pieces. Or create a shim to make the pole tip a bit thicker.
Ron Bell at MLD states that his CF jacks fit well over BD pole tips. I once I had a pair of CF pole jacks from Titanium Goat that would not fit over any of my poles. :-(