While writing my first ever Sublime Text plugin, I had a hell of a time figuring out a proper development workflow that worked for me and even searching on ST's forum didn't really turn up anything helpful.  A few of the problems I experienced were

1. Code changes not being registered by ST and thus leading me to restart it only to run into problem #2.
2. Having my code deleted by ST on restart.
3. Default settings didn't seem to be read in correctly.
4. ...

How much of my problems stemmed from being a relative novice with Python vs ST specific issues, I'm unsure.  However I will go further in saying that the thing I missed most from node.js development is using something like node's --inspect flag and Chrome DevTools which allows one to step through code as well as to inspect program state.  Without knowledge of a similar tool for Python, I reverted back to console logging which in this case included a bunch of print() usage before getting a properly configured logging setup (again, not sure which was at fault Python/ST but in this case I have a strong feeling it was ST specific as code reloading was broken).  Maybe the reader is familiar with both universes and knows of some Python tooling which is similar to node's inspect...  

At a certain point I really missed the simplicity that is my Node.js workflow, felt much like the dude above, and I even tried naively to run Grunt inside of my project working directory (Python) thinking that I could use grunt watch to reload my ST plugin on updates, which probably should work but that path got cut short when I got the error about grunt needing to be installed locally.  I didn't want to install node.js dependencies (even dev only dependencies) for a Python project.  So I ended up writing a quick shell script to solve all of my woes!  Even though I'm on Windows 10 (yeah, yeah, I know) WSL gave me the option to avoid cmd/PowerShell, etc (cause I have no desire) and go straight to the familiar shell to write this simple script watchSublimePluginDevelopment.sh which leverages inotifywait:

while inotifywait -q --event modify --format '%w' ~/me/AppData/Roaming/Sublime\ Text\ 3/Pristine\ Packages/Jenkinsfile/*.py; do
  cd ~/me/AppData/Roaming/Sublime\ Text\ 3/Packages/
  rm Jenkinsfile
  ls -la ~/me/AppData/Roaming/Sublime\ Text\ 3/Packages
  echo Detected change.
  sleep 3;
  ln -s ../Pristine\ Packages/Jenkinsfile/
  ls -la ~/me/AppData/Roaming/Sublime\ Text\ 3/Packages
done

My working directory under git control is:

~/me/AppData/Roaming/Sublime\ Text\ 3/Pristine\ Packages/Jenkinsfile

Now any changes to my Jenkinsfile plugin code will be detected by the script and subsequently reloaded by ST.  Seems removing/adding the symlink from the Packages directory works like a charm to make ST unload/reload the plugin code.  I needed to introduce a bit of a delay because without it, ST didn't notice the change.