I can't speak to why Digi isn't updating the IDE, but they are actively maintaining the libraries and sample programs on GitHub, including TLS updates and fixes for WPA vulnerabilities (for the RCM6600W which unfortunately was discontinued). https://github.com/digidotcom/DCRabbit_10
What are you doing when the debugger loses its connection? Unless you're blocking for a long period of time in a function flagged as "nodebug", you shouldn't be losing the debugger. It's possible to crash the debug kernel with bugs in your code, but during normal code execution and debugging, the debugger should remain connected and allow for single-stepping and variable watching.