When to draw the line on being "helpful"

This is the absolute, number one, key rule that must be stuck to if you're to avoid continual begging.

Willing to learn and willing to support themselves - stick with them.
Harassment, pestering and begging for help / money at every stage of the game - sever all ties, and ignore if need be.

I don't like ignoring people, but sometimes they don't accept that when you say "Enough now" that you actually mean it. Ignore is sometimes the only way to get your point across.

ill help anyone with anything, it will just cost you an arm and a leg

Simple problem. Say "no" the moment it ceases to be enjoyable to help. If they're willing to push your limits blindly, then they are toddlers in bigger bodies and you should dissociate yourself from them immediately.

The only people worth working with in this game are those that understand that all good gaming relationships are symbiotic and must be reliable. Asymmetric relationships where one person is dependent upon another don't work. They lead to resentment and ultimately collapse.

If the other player recognizes this concept and is willing to work and learn their way into a symbiotic relationship, that's fine. That's the best type of player to find - they usually blossom into competent players without ego.

If the other player has no work ethic, you need to distance yourself. All that type of player will ever do is irritate you and waste your time. Better to do it now rather than later.

Mooch: "Give me money or I'll leave the guild!"
Me (guild officer): "Good luck leaving before I kick you."

when to draw the line? when you think you are no longer helping them, but by doing things for them you are stopping them from learning the game.

I am a guild leader in a large alliance so i often help people, however one day a guy comes on and says, can you help with a mission (moddok crevice i think) so i loaded up some heroes and went to help him. when we got into the mission he was just standing there, and i told him to hurry up otherwise we would lose the person you are meant to follow at the start of the mission, he told me that he was gonna go afk while i did the mission.

I kicked him from the guild. I like to think of myself as a helpful person, but i will only help people if they are grateful and i come away feeling good that i helped them.

Giving people info is great, but again, as a guild leader i understand that there has to come a time when you just say, try /wiki it, because it will give you all the info you need and alliance members won't have to take time out to look it up themselves. Given, if someone asks a question and someone knows the answer, great, but if they are constantly asking questions about a subject, there comes a time where it is far easier for everyone if the guy just looks it up on wiki then he can get the full picture.

when to draw the line? it depends how helpful you are, but be wary of giving people TOO much help and not allowing them to play the game and work things out for themselves.