This depends on how many goods buildings you have up. It did happen to me a few times in the first few times through, but even when it did, it wasn't like the settlement was ever difficult to complete within time. Pretty sure I had nearly a week to spare even the last few times through. I'll add that on those occasions when I'm short I set as many goods buildings as I can to 4 hr productions instead of 8 to have more to collect with the chance of hitting 4x--on a longer time scale with more total productions I don't think this matters statistically, but on a short one with just a few it does.
What people consider tedium differs, of course, but I found this settlement the least tedious: I didn't need to be on every hour or 4 to try and max out productions, coin was plentiful after a day or two, expansions are easy to get, and with the obstacle removal, you can pick and chose to get an effective area to work with, and the fighting actually does involve some strategy since you can't use GBs to steam roll them--and since there are only 3/day even with manual fighting it doesn't take long. All told a low stress settlement, with a really good secondary building.