That being said, the rest is more or less true but not at all what Dervish was asking.

Dervish, sometimes the game just isn't worth the effort.

I'm only on my third character this year. Third, that's it.

I have my current character solely to contribute changes to the wiki, to enhance the ranking gear pages for classes other than warriors/rangers/assassins/thieves, and hopefully take it up to level 35 or so.

But I'm doing it as much for myself as I am for the community. Frankly, I keep fucking forgetting what gear to grab for what classes as my levels progress, and my area knowledge decays over time. Why is that the case?

Because exploration's fucking boring, that's why.

As for preps, the fewer preps you have the more you must pick your fights. The fewer concealment options your class has, the fewer fights you get to pick, and the fewer fights you have to pick the bigger and more competent the groups of people you need to pair with to survive. If you don't, the game becomes more boring than it already is for all the timesink you have between your own lack of area knowledge, what you forget about areas, and the utter fucking numbskull incompetence of your potential groupmates even the ones who you can tell in five minutes of conversation have been playing over a year or two. (That's assuming the groupmate you asked even fully committed to joining, sometimes they'll flake and give you a half-answer until they have the gear and such they need. Because they suffer from the same crap you do.)

When the game is not worth your time, it's time to re-evaluate how you're playing it. And thinking about how you're playing the game isn't just in everything Rogue stated but it's a mind thing too, how much time and effort do I really want to invest, and am I clever enough or lucky enough for it to pay off?

Ask yourself these things and then re-think if you're just better off playing something else for a while, at least for new inspiration.

For myself, I can at least add new information to streamline my gearing.