Aussie - Visas between Mexico & America

[CaptainSonny]

So I am currently living in Southern California on a working visa. I am Australian. My visa expires early next year. I bought a Catalina and thinking to spend time between Mexico & America for 12 months.

Any Aussies here (or British) with experience sailing between Mexico & America or commuting back and forth for a year or so on the ESTA? My understanding is that we might be limited being that they don't consider Mexico to be leaving properly and may reject me sailing or flying back into the country...

Any experiences?