Thanks for the replies. LionelHutz, the soft starters are Siemens 3RW40s. I've just been through a 212 page manual (big improvement over the one in the box, wasn't available last time I wrestled with these). It still doesn't explain the overload reset thing though, had to discover that the hard way. Nothing new to help find a way to wire around this issue either.
We didn't catch this in the shop because we test with an undersized motor. The trip that causes (no load) clears with power cycling so works with the shunt trip breaker. It's hard to replicate the real world OL trip, lucky I was able to mess with this one onsite in a spot where I could start it a bunch of times with the OL turned down and see the trip behavior - wired it different ways (regular run command closure with control power always on, also the alternate with jumpered run terminals and run command via control power closure, etc.), also installed a (several years newer) replacement starter. It is the case that control power must be on for 5 minutes before an OL fault can be reset.
Though we built this setup, I know we installed a factory built pump panel a few years back that had the same components (i.e. shunt trip breaker, external trip timer, NO isolation contactor). I expect that one has either never tripped on OL, or somebody figured out pulling the trip timer to accomplish OL reset - timer's probably lying in the bottom of the panel (or at the bottom of a nearby canal!). If so, now if a thyristor shorts the motor winding will likely fail . . .
I also know from experience that a UPS for one of these has to be way oversized (like 1000VA on a bigger unit, where a 250VA CPT is adequate) to be able to pull in the bypass contactor when the time comes.
So the magic bullet would be a little component array that can be stuck into the A1 A2 terminals. It must be OK to be always powered, and not cause trouble while in parallel with the load (control board power supply plus bypass contactor coil, inrush and holding). Now I've described it, it seems pretty unlikely (sort of a reverse snubber, probably zap the board).
I guess the options are the fat UPS (with guaranteed battery failure in a couple years), or some miniature capacitor version to be swapped into A1 A2 via relays at power off. When power is removed (via shunt trip)it needs to supply the 120VAC circuit board power only for the 5 plus minute thermal timeout, so when main power is restored the thing can be reset. It's OK if it peters out, probably cause a low volts fault but that's cleared via power cycle anyway. Then we just tell the user to always wait the 5 minutes, then push reset immediately after resetting the breaker. Then if it WAS an OL fault they can run again, but if there's a (non-resettable) device fault like the failed thyristors the short timed shunt trip will protect the motor as intended.
I know an isolation contactor would take care of this, of course, but hate to give up on this arrangement - seems tantalizingly close to everything we need without the extra expense and panel space . . .