Here are some tips for the achievement:
1) Your choice of partners is important. Better opponents will forfeit when your initial roll is a lot better than theirs. Easier opponents seem to stay in the game even if it's clear they're not going to win -- Zindrab in the inn in Chapter 1, for instance. At first, I was trying against a woman just outside the walls, and she'd often forfeit even if my initial roll was 3 of a kind or better, making it pretty much impossible to get the achievement unless you roll 5 of a kind as a complete re-roll on your second attempt. Zindrab stayed in when my first roll was 4 of a kind, letting me complete the set on my second roll and get the achievement. Any of them at the table in the Inn's basement will probably work, but if you're past chapter 1, try with the lowest-ranking dice players in each chapter.
2) I was using the corner-stacking trick when I got the achievement (ex: see the video from the first solution), but I don't know for sure that it helped. The initial placement is random, plus it takes longer to drag them down to the corner, so each attempt is going to take that much longer and they'll probably only stack the way they first entered the board anyway. And even stacking them, one or two will probably fall off the top of the stack when you release (if they're even positioned to stack at all). Although, the initial placement does seem to be less random than just rolling from the middle, so it's possible that stacking them might give you 3 or 4 on the first roll more often than a random roll, making it worth the added time to set it up each time. Your call though.
3) As other have said, you don't need to roll 5 of a kind at once. And even if you do (on your first roll), you don't get the achievement. The "trick" is that you have to win the match with 5 of a kind. The danger in getting 5 of a kind on your first roll is that your opponent is probably going to forfeit, denying you the achievement.
4) Don't mistake the 5 dice for the 6 dice. They're both stars, but one is a traditional pentagram (5 sides) and the other is more like a Star of David (6 sides).
5) If you have no matching dice, you might as well re-roll them all. Otherwise, keep the ones you have the "most" of after your first roll, and select the others (with X) to be re-rolled. If you have two pair, just stick with your favorite pair because it's probably not going to matter.
6) Some have said this is a good way to earn extra money for trying for the achievement, but it's a slow process to keep reloading each time you lose. I'd recommend just getting a fair amount of money to start (a couple hundred, maybe), then always betting/raising the minimum. If you Pass, you automatically lose, so don't do that. Save before starting for the achievement, play until you run out of money, and only reload if you're broke. Once you get the achievement, reload if you have a net loss.