I have never played D3, so I can't make a direct comparison to that, but in general D2 drops things quite infrequently. Most of my characters have historically ran with really low key gear. 1 or 2 nice items, supplemented by a rag-tag mish-mash of magics and rares. I think your expectations are set too high. Getting BIS (best in slots) in all positions is something that will probably take years. When I read item recommendation in a guide... Well I usually stop after 1-2 slots, cause it's all high tier stuff I might never get, and definately don't need to play the character. (And if I do need it, I will just play something else.)
Further, when you run something try to not focus on finding
that one thing (or handful of things) - that will only make you disappointed, and miss all the other fun stuff you find. If I look for a
Griphon's eye, chances are slim I will be happy. If I look for
nice things in general in this spot that sometimes drops a Griphon's eye, I can more easily appreciate the bases that drop, the fun jewels I find, the rares with crap stats but fun/cool names.
This is a consequence of how our brains are constructed (I forget the name of the actual bias...), where we tend to see what we focus on. Focus on one item - you only see it not dropping and miss out on all the other nice things. Focus more on broadly (or keep an open mind), you will see all the pieces of silver even if you don't strike gold.
My ramblings above are unimportant though; here is my actual advice. Find a way to play the game that you enjoy, that is not based on RNG/drops or other external factors. If you don't enjoy pit runs et. al., running them will only lead to frustration. I have slim patience for things like LK/repeated meph runs etc. While I do run them occationally, I usually keep the number of runs low before I go do something I enjoy more. What I enjoy the most tend to be questing (at least from about normal A5 and onwards), and so I tend to start alot of new characters. That is what is most fun for me?
So please
@Goomba, tell me: What do you think is most fun about Diablo II?