MegaWaffle

Only thing better than games are free games.

Those two ideas you have that aren't possible vanilla are worth developing fully as a side mod, maybe.as a sort of "Sim Settlements - F4SE Addon Pack", or even as it's own mod separate from the SimSett family. Auto-equipping settlers especially would be outright amazing, F4SE or not.

I don't mind it's new look. Although I'd prefer if you'd tighten up the extra space to make the page cleaner and less spacious areas around text, but that's personal preference in aesthetic. Looks good overall I think.