I gave it a shot and it seemed to work pretty well, although I did make a couple mistakes. Live and learn.
You've moved yourself far along. Now you have an experience base from which to make future adjustments.
I also wonder about the oxygen in the tube from the spigot to the keg. I initially opened up the spigot and tried to fill the tube with beer, before hooking it up to the keg. But I guess physics didn't like that idea, so I saw an air bubble flowing up the tube and into the spigot. I introduced some oxygen to the beer before it even touched the keg.
Yep. So the question is, how are you going to address that? One way is to allow the tube to fill with beer and vacate the tube of o2. Or you could try this:
After I purge my kegs there typically is a little CO2 pressure remaining. What you can do is hook up the QD to the gas side before you connect the tube to the spigot, and let that residual CO2 purge that tube, then as it gets to almost no pressure, direct that into the spigot without connecting, and then when it's essentially done, connect to the spigot. Voila! Purged lines. I favor this approach when transferring from a spigot.
When I pull beer out of my conical, I'll attach the line to the fermenter then use a jumper that opens up the QD that attaches to the liquid OUT post, and let the beer flush air out of the tubing. I use the butterfly valve to shut it off, remove the jumper, attach to the keg post, and go.
Overall it seemed to work well. If I looked at the keg at the proper angle, I was able to see a condensation line going up the keg and that let me know how much it filled up. I rarely have enough beer to overflow a keg, but the condensation line would help prevent that from happening if I wound up with a little extra in the fermentation bucket.
This is one reason why I like to crash my beer before packaging. I'll almost always get a condensation line on the keg as it fills, so easy to monitor progress.
The only downside to that I've found is when my garage, during the winter, is too cold and dry. I've finessed that a bit by boiling a half-liter of water in a beaker and letting the steam from it condense on the side of the keg. Works fairly well though not perfectly well. In the future I've decided I should warm the side of the keg with a heat gun so the line is more pronounced. Once or twice I've lost enough focus to have the beer come out through the spunding valve. Then I have to disassemble that and clean it.
I've tried the "weigh the keg as you fill it" approach but that's failed every time for me. Usually the scale turns off before the keg is full, and there you are. There are ways around that but I've found them futzy. The condensation line is better for me.