I use a combination of Adafruit Ampy to copy files, esptool to reflash, picocom for the REPL, and VSCode. Some of those might be redundant and it did take a bit to figure out the syntax. But once that’s determined it’s cake, and all saved in my CLI history. I just Ctrl+R and bring it back.
For ESP32? You just install the VS Code extension and it does all the toolchain setup and you can flash with a button.