I dunno why anyone would ask for help on a forum where they're going to praise their product and pretty much make anyone feel stupid who doesn't understand it. You shouldn't need to take a Class to completely re-learn The Basics of Load Order setup...... because some app dev "says" they know better than you do. Yeah? well your program took my perfect load order and put ESPs inbetween ESMs... Mods loading BETWEEN DLCs. No, the drag-a-link thing doesnt work. Setting rules doesn't work, i actually set "A must load after B" for EVERY single file.... yet that doesn't work either.
Yes I'm new to this, so rag on me for it! Or, your concept might be good, but the way you are presenting it to people is not. f*** your LOOT. Mod Organizer here i come!
Both .esp files loading between .esms and plugins loading between DLCs are valid scenarios.
LOOT or Vortex's integration thereof is not one app dev thinking he (I'm assuming you mean me?) knows better, there is an entire community behind creating these rules, most of the hard rules are mod author instructions turned into automation rules.
Finally: I've been modding bethesda games for ~10 years, you admit you are new to this, so is it really such a weird concept that I might know better than you? Do I really have to feel bad for assuming that 10 years of experience means something?
We're always happy to hear constructive criticisms that could help our presentation but I think in this case the problem isn't our presentation but your incorrect assumptions on how plugins work, like that .esps can't be loaded between .esms.
With MO you may be more able to get the order you think is right but that won't change the fact that you're basing it on incorrect information.
You could have taken Vortex loading esps between esms and thought "hmm, maybe I misunderstood something, maybe this is valid. Oh and would you look at this, the game runs fine." and then you would have learned something. Instead you naturally assumed you know better even though you have absolutely no reason to think that and didn't even bother verifying it.
Now you use MO which lets you continue to dwell in your incorrect assumptions and propagate them to other users when you tell them "this is how it works, trust me, I have entire months of experience".