Hrm. Introspective moment.
For me, I struggled with a few things. There are my opinions on the "social game" that I've mentioned in a few other posts so I won't expound here.
One thing that was always difficult for me was the concept of plotting and planning. I always wanted to plot and plan without detailing ahead of time everything I was thinking of doing because doing so always made the RP feel railroaded and overorchestrated to me. So I'd have an idea, play my cards close to my chest, and run into some OOC issue because I didn't detail it ahead of time; which I didn't because something felt non-gamey about getting "buyoff" on what my character would do or outline everything that was going to happen, thus giving other players the ability to ponder SUPER PREPARED RESPONSE to things I wanted to do. At that point it always felt like getting permission to do what my char would do, so it was a balancing act that I would probably still struggle with today.
I like being able to have surprises to unveil, and I like to be surprised. Overplanning and detailing things Oocly beforehand kills that. My characters, to me, were less of an investment and more of a replaceable element.
For me, I always viewed these games as "RPGs with some writing" rather than "cooperative writing in an RPG backdrop", which explains my preferences clearly. I always wanted an online space to play VtM/WoD/etc, but mushing isn't exactly that. Hindsight being 20/20, if I could do it again, I probably would prefer to have come to that understanding sooner rather than to pluck the chicken for 10+ years.
Not sure how I would tackle this if I played again. It's something I think about when I consider redownloading Potato.