Looks like a good start to the settlers’ XP system (I hope they keep their XP with previous jobs when some kind of job reassignment is implemented!).
I’m not sold on the town XP though. To my mind, there are already two XP systems for settlements:
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Net wealth, which causes various other things, eg bigger goblin raids.
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New settlers, which lets you get more specialists, effectively dealing with the tech/perks/bonus side of things in the new XP system.
Personally, I’d stick to just the individual settlers’ XP system… with one exception:
Eventually, I assume we’re going to have a more regular method of getting new settlers, rather like the periodic migrations in Dwarf Fortress or Gnomoria. In that case, how about something like this:
So for example, the 3/10 bars here might mean just a handful of basic peasants - maybe one or two have some starting proficiency in carpentry or w/e, but it’s not special.
On the other hand, a 10/10 migration means not only some awesome settlers, but also that you’re doing really well - you’re fending off the goblins, people are happy etc, and so your settlement is a popular destination.