I was going to say, "Hey, how about starting an induction motor", because I think Midnight's 4x DeWalt compressors were brush type. But good to see your Ingersoll Rand is an induction motor. Better stress test! What are the ratings on its motor?
You described the low-frequency Schneider as using relay to disconnect load from inverter, reconnect to grid, and said benefit of high-frequency inverter such as Rosie was it just connects (without dropout.) There are low-frequency inverters that also synchronize and connect with SPST relay.
Disconnect grid at the pole so you can backfeed to compressor from inverter? I'd rather it was properly interlocked. (Yeah, I know, "Trust me, I'm a professional!")
Good to see you're giving Rosie a tough test. This compressor is obviously a bigger load than the well pump (which would be the critical load for most customers.)