Well, I just got the 2019.16.2 update. On the way to the store, I noticed on the Software section it indicated it was downloading an update but said I needed to connect to Wifi to resume the update. It was sitting at ~5-10% (just a very small portion of the progress bar filled). After I got home, I verified I was connected to wifi and after sitting there for about 10 minutes, the progress bar didn't move even though it said it was downloading. I run an Sophos XG firewall so I assigned the Model S to a firewall rule that bypasses everything, even though it's never been an issue in the past, and rebooted the MCU. After that, it started downloading and got to about ~90% percent and stopped again. I let it sit for about 30 mins but nothing happened. I ended up rebooting the MCU again thinking maybe it got stuck but that didn't do anything. After about an hour, I got a notification an update was available.
All that to say, not sure if my firewall was an issue because it never was in the past (maybe just coincidence when I restarted the MCU). It also appears the download might look like it's stuck at almost completion and sit there for a while before you get an update notification. It doesn't look like "Advanced" made much of a difference for me. I'm still receiving the latest update about 1-2 weeks later when the last bunch gets pushed updates based on watching TeslaFi.