I normally don't pay attention; I just do a quest here and there and then I get an Open Trade Routes quest some day, and then at some point I have tier II quests available without really knowing how I got there.
In my current game (day 8 so far) I had an Open Trade Routes from Hugh in my quests list, so I decided to pay attention this time (I play 120 minute days, so that's one reason it took a while to reply). My reputation with Hugh was 5. I did the quest and, and after having to wait to the next day, then 5 more fetch/clear/buried quests until my reputation with him was 10.
When I handed in the last quest, I got a console error (screenshot below), so I don't know if that has anything to do with things turning out how they have, but I didn't get the tier II reward, and the next day I didn't have tier II quests either. I did another quest, just to see if it changed anything, but it didn't.
So maybe there is a problem.
I'm
reasonably certain I had tier IIs in my B23 game (but I'd done more Scout quests in that game than I have now, so I should maybe see if they affect things).
EDIT: I got the Scout faction up to 10 and then did random stuff for a day or a bit more, took a clear quest (tier I) from Hugh late in the day and did it the next morning and now he has tier II quests. Hugh is at 13 now.
So I don't know if Scout reputation matters or exactly what is going on, but it is possible to get tier IIs.