I would recommend against a realm transfer based on what I've seen from guilds who leave my server. I'm stuck on a low population realm, where many of the larger and more advanced guilds have departed for greener pastures on higher pop realms. Even before character transfers it seemed that every year or so the top PvE guild decides that they've grown too big for my server, citing many of the same problems that you did: difficulty of recruiting, sucky economy etc.

Let me tell you something though: not one of those guilds lasted longer than six months on their new server. Sure, small sample size, but every one of those guilds that left, often with middle fingers waving at this backwater server, has stopped raiding completely.

I can only hypothesize about why the transferring guilds broke up, but:
1) You have no street cred whatsoever when you join a new server. Why would someone want to join your guild when they can join an established one? Not to mention that after the transfer you're likely missing a good chunk of players, so starting anew may take a while. On top of that, no longer being top dawg on the server will create morale issues.
2) A lot of raiders may simply be burned out on the game, and they think life on another server might be better when really they're just tired of WoW.
3) (And this one probably doesn't apply to you but bears mentioning) Frankly, the leadership in some of the departing guilds were a bunch of dicks. People may have been stuck with you when you're the only progression guild on the server, but when there are options don't expect them to tolerate assholery as much.

So yeah I would advise against it, but if you do pull the trigger be sure to come back and tell us how it went!

As for raid leading: give it a try! You're fearing rain and there isn't a single cloud in the sky- your fellow raiders seem to think you'd do a good job. Worst case scenario you give it a try, it doesn't take, and you graciously bow out.

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