Thank you so much for your in-depth response! Seriously, I didn't actually expect to get replies with how long my message was and how little I thought people would care. xD;
I very much appreciate it and it actually helped out quite a bit! One part that especially stood out was about having gone through Hoenn multiple times. It definitely never crossed my mind that, because of how much I played it as a kid, that contributed to why I wasn't feeling all that excited of going through it again after already having done so a handful of months ago.
After some intense thinking and then reading your response, I was actually ready to [reluctantly] delete my save file for XY and start anew! However, I received a phone call from one of my best friends yesterday before I could. He and I actually played BW/B2W2 when they were first released back when we were in College! We considered ourselves "rivals" and played the game as such, constantly challenging each other and just having a blast with it!
Gen 5 actually holds a very close place in my heart, something I didn't quite realize until I got his call yesterday. Gen 3 may have been the one I played obsessively as a kid and have the most memories of, but Gen 5 was the first time I ever had someone to play the game with alongside me [that wasn't my sister], had someone to play with as "rivals", and even got me into competitive battling! Unlike Gen 3, however, I've only actually gone through Gen 5 once, so it's interesting to think that it could very well go up against Gen 3 in terms of favorite if I were to play it more!
In any case, my friend has just recently gone through a pretty bad break up with a partner of 3 years. After talking for a while I told him about my huge Pokémon mood and he told me he had actually gotten into one, as well, about a week or two ago, but he hadn't done anything about it 'cause "everyone was already done with Pokémon." [As in, everyone from our group of friends had already stopped playing ORAS and the hype had died down.] I told him how I was debating replaying BW/B2W2 and we ended up talking about for over an hour!
So, we decided we'll both be going through BW once more! I think it'll be extremely fun to sort of relive those College days, all the while having someone to play it with and give him something to distract him and keep his mind off things! I'm sorry that after writing all of that I ended up going with something other than what you suggested. @.@ I did, however, very much agree with everything and had my mind set on XY until I got that call!
Once again, though, thank you so much for the response. I hope the length of this one isn't a bother, either. xD;
[Sidenote: In regards to the Pokédex, what I've decided to do is that since I have Black and he has White, we can both try to at least complete the Unova Pokédex rather than the National one. It'll definitely still feel very satisfying, since I haven't completed any Pokédex yet, and I can then focus on the full thin on ORAS! Without having to replay the game, too. [Granted I'm still in a huge Pokémon mood, but yeah!]