Cartwheels looking pretty sweet.
Have you tried bailing from a wall based handstand? Much easier and might give you the feedback that you need. Also, I dare say that if you can't hold a freestanding handstand then any bailing is going to look kind of ugly.
good point about not being able to hold a freestanding one. i can, a little bit, but can't really kick into it consistently. think i need to just treat handstand bailing as kicking into a freestanding handstand and then coming out of it under control rather than the weird quasi-cartwheel thing i've been treating it as.
What are you training for?
Some kind of gymnastics? It's super fun to integrate into training, as athletic as you are handstands, front tucks and back tucks and gainers are super easy to get in a few months. I used to mess around with a bunch of tumbling, I still do backtucks and front tucks but gainers and twists are scary and I need to refresh them on forgiving surfaces before attempting them on concrete. Def good skills to get...
As far as the handstand bails, the problem is that you are not actually doing handstand before you bail...
This can be fixed w two things.
More time on the wall to figure out the hands. The balance is in the hands - push harder to go back and release pressure to fall forward... you have to get the feelin in the fingers for this.
For the bail you have to bail AFTER you lose the handstand rather than before. To do this you need to learn to forward roll out of your handstand. Start slow w basic hopping forward rolls but you quickly will be able to hold your handstand and fall forward and then as you are losing it tuck your chin to your head and roll out of it.
To do this right you want to also release your elbows so they bend as you forward roll... this will be hard at first but it's ok. Initially you won't lower yourself into the forward roll gracefully so it will be more like handstand - fall onto upper back - roll out. Not pretty but on grass it won't be painful or dangerous as long as you keep your chin tucked...