Of course, for most people, it probably gets a lot easier a lot faster than it has for me!
It's been about 4 years, but as of last night, I got to the point in my automation where I only had to do a polar alignment and lock in good (starting) focus. After that I went to a show downtown and set SGP to start at 8:05PM.
The target solved, guiding was fantastic (.46 Total RMS), and I got half of my subs before I even got home. Just needed to check focus a few more times before clouds rolled in early morning. Now I'm just downloading my files from my NUC and enjoying a cup of coffee!
Still plenty of minor tweaks to mess with, but at this focal length at least, I'm feeling very good about going into winter comfortably, which means very few excuses not to set up when it's clear outside
Thanks for all your help folks!!