My kids is 4.5 and I really didn't have to do anything. I sat her in it, showed her her how to sit properly, routed the belt around her, and buckled. I explained how she needed to sit and how she coudn't lean forward or to the side. Basically, I told her to sit back with her head between the wings for the entire trip. Then we took a drive to the supermarket, which is like 1/2 a mile away. She did great. And, uh, since I had just been in a wreck and didn't have a replacement harnessed seat for her, the booster was it. She rode around in it for a few weeks with ZERO problems. I know she's on the younger side, but she's got great maturity and didn't need ANY reminding to sit properly for the few weeks until I got her another harnessed seat.
My theory is that booster-training is like potty-training. If it just seems harder than it should be, you're probably right. It's best to step back and try again later on. When the kid is ready, it goes quickly and easily.
The one thing I've noticed with long-term harnessed kids is that when they get in a booster, they're so used to not having to worry about what the car is doing that they're more likely to tip with curves, because they're not actively keeping themselves upright (and hence keeping the booster sat upright, too). This has happened with a couple of friends, and all it took was pointing it out to the child (7-9 year olds, in these cases).
I mentioned the Clek Oobr in my first post. It's latchable, and it fits small riders well.
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