So as I was playing I came across a trainer. (no its not the first time) Anywho, I Decided to take advantage of the services offered. Upon using these sevices I came to the conclusion that I dont like having to go back to the dialogue (spelling?) menu and select training every time. I know im just lazy and it doesn't take much time. But I would like it to be just clicking on the training I'd like to recieve until the trainer cannot train anymore or until I reach the point i want to stop without seeing the dialogue (again with the spelling) menu again. Can it be done?

I don't know if there is a simple way to do that. If not, I recommend just aligning the windows so that you don't need to move your cursor at all and using one of the multitudes of free applications that do rapid-fire clicking for you so it's less tedious. It becomes very, very annoying though when your instructor decides to wander around in which case you may want to go in and edit those NPCs to not wander.

I think, ideally, for people who play with vanilla rules and are thus able to afford massive amounts of training, it would be nice to be able to purchase training in bulk.

Since Training is done through Dialog, the normal method of Training is likely hardcoded into the game to function in this specific way.
Making these changes would likely be impossible, except maybe with MCP.

You could completely remove it from dialog and add it as a script to an activator. On click, time passes, skill experience gained, cash taken away. The cash part might be difficult to do fairly, as the normal training fee draws from a lot of things. Or you could do something with force conversation to ask the PC if they want to continue training. Not sure if that's possible, but it's an idea.

I wish that some one would make it possible for the training money is added to the merchant's barter supply rather than the black hole.

Well, you can do that with Dialog... but unfortunately the game only records a Skill increase as experience towards your next level if it is earned through action or Training. An increase in a Skill through Dialog or scripting will increase the Skill, but not count as actual experience earned.... so it kinda defeats the purpose.

So, it would seem as though the universal concensus here is that this simpley cannot be done?

Oh what about maybe a script that overrides the game kicking you out of the training screen. If i'm not mistaken morrowind on the xbox did not kick you out of the training window until you pushed ok or whatever. But, it has been many years since i've played that.