RyaReisender: To be fair, I didn't measure the time I played it, so it's just an estimate. But I thought it was around 10 hours playtime until you've visited all cities and the "war" starts. After that felt like it was pretty much the last thing added. I could only take the same contracts again and again in endless loop.
Considering that the "end-game crisis"
occurs between 80-100 of in-game days, it definitely takes much longer than 10 hours. I guess you could hit it at around 30 hours, but then I'd assume your band to be unprepared to handle it, since it would suggest you did not aggressively pursue either contract or exploration battles.
RyaReisender: Not at all, I actually really loved the game until I reached point where it felt repetitive. The problem is I'm doing contracts in town and save them, but a bit later they get attacked or something else happens and then you have to do very similar contracts again. It feels like you are in an endless loop of hopelessness. Same about the war. Even if I focused my help on a faction and was successful, it still didn't seem to end up with that faction winning. The enemies always kept fighting back and won towns were lost again. So it just ended up feeling like a completely pointless task. Just doing the same things again and again without hope.
I guess that's just the nature of procgen games - sooner or later "new" things will run out.
Although
there are quite a lot of different contract types, and they are further varied by enemies you'll encounter (which ties to both contract difficulty and game progression).
RyaReisender: I wonder how much use I can make of this. Already before the DLC, exploration was really hard because you'd need a lot of resources like food and arrows stored to be able to venture really far.
To be honest, I've never seen it that way. More like soft-cap on your ability to access more difficult content.
You can still easily explore within a few days' range from settlements (assuming, of course, that you are already past the early-days "must get money to feed everybody and repair things and equip them a bit better and oh I'm out of money and food" trap :)
Considering that exploration was already better rewarded than contracts even without the DLC, I would switch to it between 30-40 days in (or, if RNGesus was with me, in mid-20s on occasion). Anything close to settlements was usually pretty low-level in terms of enemies, anyway. I usually end up looking for and raiding bandit camps to get Mail for my brothers, especially since Worn Mail is unlikely to be found in stores, and works quite well as mid-level armor for ranged support types.
But it's not entirely "blind" exploration, either. I generally go by rumors, or do a short sweep through wilderness if I see several bandit groups roaming about.