We had some serious struggles when we first started. We started out in Balanazaar . . . as Alliance. It's PVP with something like 80% Horde. It was awful, BUT we learned how to PVP like maniacs.
I hit terminal in vanilla, and Lisa hit it in BC. We tried to get into a guild, and all I heard was "are you attuned, yet?" And if you weren't, they wouldn't even talk to you. We didn't have many terminal friends, and the ones we knew weren't, well, they just weren't really that good. It was REALLY tough for us to get through the three (I'm going back into my memory) instances to get attuned. Dude, I still hear "TIME FOR FUN!" in my sleep! LOL! It took us, no kidding, a couple of months to finally get enough good groups to get through. In true anti-climatic manner, we got the very last instance with a group that just happened to be there. We went with a group, and they were terrible. They quit, and we were outside the instance. Three toons were there, and we talked to them. It was some "guildies" running a new guy through to get last of the attunement. They were going to THREE MAN IT . . . but said we're welcome to come along. I laughed because five couldn't do it so NO WAY could 2 good players and one about like us do it. Sheeesh . . . like 45 minutes later Lisa and I have completed the instance with them, and it was like "meh . . . I didn't even fight the last boss fight".
We got attuned and got into a guild. We did the first raid with them, and it was PAINFUL. They were all jerks, and since we weren't experts already, we got dumped. Then we got into a really laid back guild with some good players. They really helped us out, and they were patient. Lisa got REALLY into it because they raided slow, methodical, and they explained things to her. Once she got some gear, she was in friggin' demand. There were practically zero shadow priests, and she was pretty geared. Mages and locks in the guild got to where they'd only run with her for the manna. My hunter got geared up, and then they found out I had a tank. They bum rushed him for gear, and then I was tanking. We were pretty hooked then.
The next expansion came out, we got terminal, and by then we were in a new guild. These guys were serious. A bunch of them were either retired old dudes or people home on disability i.e. they played, literally, all day long. We had to work hard every night just to keep up with all the crap we needed to raid with them. They just got too demanding, and Lisa got fed up one night. Oddly enough, when I "saw it all", I agreed, and we pretty much have quit.
I played some vanilla, but I haven't in a while. My son still plays retail, but not nearly as seriously. Honestly, it's lost a lot of the complexity and challenge, so it's not that big a deal, anymore. Another thing is that, eh, a lot of the social aspect is gone, too. LFG, at first, was like the most wonderful thing ever. After a while, though, you star figuring out that being in a guild isn't a big deal, anymore, because you can do everything through LFG that you used to rely on your guildy friends for. That's probably one of the main reasons we sort of quit.