I think this really does involve a metric ton of learning by doing - and then redoing - and then relearning. It's such an iterative process, I don't think you could really shortcut it. If you tried, you'd just hamstring yourself long term as each time you hit some barrier, you wouldn't have the background knowledge on how you solved it before. You really need to learn the foundational stuff yourself - and there's no better teacher than repetition along side experience and trial and error.

There's also a fair amount of figuring out when good enough is actually good enough and when it isn't - that largely depends what exactly you're trying to do in-game. There's almost always some way you can keep improving your setup. But many of us get to the point where what we have is working well enough for the content that we enjoy doing that we don't bother.

As slow a start as it may seem, its not that bad. Create some level 1's. Figure out how to get your basic movement down in the starting zone. Then dig into some basic combat (still in the starting zone). Before you know it you'll be questing away and feeling pretty confident. Then you'll run your 1st dungeon and realize everything you thought you were doing OK at isn't really good enough and you'll iterate again.

I'd go so far as saying that if you don't enjoy this sort of iterative process of continual experimentation and improvement - then multiboxing may not be the sport for you.

-----------

That and I think this forum in particular tends to folks much older and much better off financially than the standard WoW forum. My guess is that many of us here are middle-aged professionals. Your offer of financial incentive would probably go much further in other circles. Its kinda like why I brew my own beer - its not because I like cheap beer.