In Skyrim I did finally get the three remaining achievements that I believe to be possible at this point, but unfortunately it is going to look like this playthrough is coming to an end. The reason for this is simple, to level up the werewolf skills, you need to kill and eat humans, at least at the start.
The first thing I did was get married, which was super easy. Then the next was how to handle this werewolf business. I decided to do the pickpocketing since I still needed to do that, and figured I would pickpocket until caught, then turn into a werewolf. Now there are a couple of towns that have no population left. Sorry game. I did manage to finish up the werewolf skills before I got 1000 bounty in every hold. Then I switched to just killing guards, and the hard part was getting arrested after getting that achievement since guards will be on kill on site mode. I did eventually find someone who tried to arrest me, rather it turned out I found a Thieve's Guild person who I bribed to remove the fines. Now I'm not sure if it was just the fines in that one hold or not.
The only feasible thing left to get is the pickpockets. And then I think I'm just going to add mods until the world breaks. Then I will redo the mods I have installed and start a new game where I choose the side of the Imperials, and try to get the remaining achievements.