I've tested this with a savefile with seven skill points to allocate with all the new skills selected. None of them when maxed reward the achievement. Playing For Both Teams also doesn't seem to work, since I've played and died as both male and female several times to no avail before and after getting the DLC. You Used All The Glue on Purpose also doesn't appear to work, since I've used the lathe 500 times and nothing was awarded, this on a savefile after the DLC was downloaded.
It gets better. All the counter-type achievements that I hadn't got yet (e.g. The Critic) appear to have been reset to 0, and are not incrementing. Edit: No, they are incrementing. But they're still doing so from 0.
The counter achievements have always just reset themselves at seemingly random well before the DLC. The solution I found was just complete the achievement in one clean shot, takes a few hours if you have the time to kill, but it can be done if you're okay with constantly reloading savefiles after murdering yourself to remake potions, kill diggles, get cursed by Krong etc.
Also, the You Know What Time It Is achievement works, so evidently the issue is not a general DLC issue.
Those items and subsequently the achievement was achieveable before the DLC was released. I should know, I DID get the achievement before the DLC came out.
I've maxed out piracy, werediggle, big game hunter and killer vegan without getting any achievements. I did however get Loyal Soldier of the Empire for equipping the Imperial boilerplate armour.
I went to go and confirm this for myself and yep, it does look like that one is working, so I can remove that comment about me assuming the rest won't work because of the others being bugged. I'm a go get myself killed by a Muscle Diggle just to check if that one works or not.
Just got killed twice by a Muscle Diggle. The achievement isn't popping for that one either. Seems that ONLY Loyal Soldier of The Empire is working out of all the DLC achievements. Then again, I have no idea if Playing for Both Teams or You Used All The Glue on Purpose were even DLC-specific or achieveable but bugged from the get-go, since the requirements were completable before the DLC but their place in the achievement list seems to suggest that they're DLC-specific.
"Diggle Nog!" and "You Know What Time It Is" work both for me. "Team... Jacob?" and "Playing For Both Teams" don't.
