Deprecated in microcontroller land means you should probably move away sometime within the next 10 years or so. And being on the bleeding edge can be quite painful. So I think Xtensa based ESP32 was a good choice, for a first board. It will have the best support for at least another 3 years. And possibly way longer.

Also, arguably the entire Arduino brand started on a deprecated (and much less capable) platform, the Atmel AVR8. It was not an issue either.