Well, I think you are for some reason avoiding the obvious answer that this is simply how it is designed.
Thats all there is to it. The engineers put a million weird, bizarre rules into the software that governs the entire vehicle and this is one of them. Can't tell you why, because they don't care to ever explain any of it. The dealer cannot tell you why, because FCA does not tell them. FCA chat/email support cannot tell you why, because they don't get told sh!t either. They let these nameless engineers put all this complex programming and huge matrix of conditional rules into the vehicle software, and then they disappear, never to be seen or be asked to explain what they did or why ever again.
None of the support drones us common peasants are able to contact at FCA have any ability to reach out to an actual FCA engineer and ask "Hey, so, we see this interesting behavior and we were just wondering what the reason for it is?" Hence, you won't get any answers. All you can do, is observe and note the behavior and try to work around it. The dealer has absolutely no capability to do any modifications of any sort to this software. The whole software package comes from the FCA engineers, all they are able to do is plug in a cable and install the entire package. No modifications or customizations are possible.
So, it is was it is. You have to just live with it. This is not the only random remote start behavior I have observed. If you spend too much time dinking around after you park, if you take too long to lock it up because you are opening other doors and unloading groceries or something bogus and then you lock it and go to use the remote start the next day, it gives you the same damn "Remote start disabled - start vehicle to reset" crap with no explanation.
Its frustrating but there is nothing we can do.