I'd like to see this thread become a place where people can ask this freely without judgement or flamewar erupting. I'll post first.

Is it an exploit to go to a trainer, pay them for training and then pickpocket the money back?

I say it's not an exploit but a part of the game, if you're gonna play a thief why would this be out of bounds? If it were something the devs didn't want to see happen it wouldn't be tough to just make the money you pay a trainer go poof rather than land in his/her pocket where it could be picked.

I have a very simple view of what is and isn't an exploit, if it's something that could happen in the real world of Skyrim, buy something only to steal the coin back for example, it's underhanded perhaps but not an exploit. The line for me is crossed when you open up the console and type something into it in order to gain something. To me that's not playing the game, but rather, playing with the game. And there is nothing wrong with that if that's how you want to go about it, but it's an exploit.

Thoughts?

Feel free to post your own little thing that might be construed as an exploit and your justification for why it's not.

not at all. because not only have you bought lessons, you have improved your own skills by using them. no different then if you were to steal money from some random person's pocket. it just so happens this person has your money.

I do this often with my thief characters, and only with my thief characters.

If its not in my character's nature to steal something then no, I don't steal it back.

But its not an exploit.

I do it all the time. The "extra pockets" perk is one of those must have perks all my characters get.

What I do consider an exploit is save scumming in order to never fail the pickpocket attempt...even if it's a 1% chance.

Wow, that's an aspect I never considered. Yes, saving to ensure you don't fail the pickpocket is an exploit of sorts, but then you'd also have to say that saving just before a big fight is also a save scum as well. I mean if you know you're about to get into a hard fight, saving just before it starts to ensure you don't have to re-do the whole dungeon can be looked at the same way don't you think?

Well, you know. Single player game blah blah blah do what you want.

It's basically up to you to decide what's an exploit and what your character will or will not do.

I would consider paying for training to be a feature too, even though I don't personally use it very often. An exploit (at least in my mind) is using a "bug" in the game to do things that were not intended by the developers.

Thats why I play Dead is dead

Similarly you can scam your followers if they are trainers! Please Faendal so he's your friend, then buy his archery training, then, as a follower, dig into his inventory and take the cash back. Rinse and repeat upto archery skill level 50. But this is even more of an exploit than stealing from a trainer who's no friend.

I guess the question is How despicable do you want to be?
Balancing the other side of the coin however, its true to say those trainer npc are real rip off merchants arnt they. Especially as the skill climbs a bit, I mean like well over a grand for just one point of training skill, so maybe they deserve a bit of scamming pay back huh!

Skyrim's not exactly like the real world of course, and you can do all sort of things that in real life would get you either arrested of punched or worse. I mean would you steal from the wallet of a martial arts instructor and then have the stones to go back for more training, pah! I think not. So my friend it all comes down to what you think is acceptable behaviour in a RPG sense, would your thief steal from his mates, his grandmother, the orphanage? But some npc's positively need a good turning over, like Belathor for instance, ok he's not a trainer, but I'd scam that slimy git even if it was his last Septim and he was about to be evicted for not paying the Jarls tax.

Sorry, right back on track, it's it an exploit? Well here's your definitive answere according to, well, me!
If it's just a trainer, not a mate, and you are not going back for more training, or he's so thick he really wouldn't notice, then .......No it's not an exploit cos you could really do it in our world if you chose to. You know, get guitar lessons then steal the guys wallet on the way out the door!

If the trainer is a friend, then yes it qualifies as an exploit cos you wouldn't really do it, and if you did , he would notice it and never invite you around for milk and cookies again, like ever!

Technically, like BlackPete said, an Exploit is a coding error that allows things to be done that should not really be possible, but they got through the Dev testing. An Exploitation glitch is even worse as it's essentially broken code that fails to prevent a cheat. Eg, the scroll duplication glitch in Oblivion. In skyrim we have the Restoration Exploitation for making Super Potions leading to things like ten thousand percent increased weapon power, if you want to go down that route, personally it's not for me.
So by that kinda definition, stealing back coin, which is a pickpockets Normal function, is Not an exploit

Ahhh, but would a friend charge you in the first place? Some friend!

Yes of course they would, it's their job. I have real mates who are builders, now they normally knock a bit off the quote for me, but they arnt going to work for free! Even for a mate, they still have a family to feed ya know and you can't expect someone to turn away paying work just to fit your job in and do it for free.

So yeah, Faendal would reasonably still expect payment for training, he's a friend not a sap. And if you think about it, he gives you like 20 gold for your help with his problem, so that's its worth. But you want him to give you like 500 golds worth of training now for free.
That would be like, maybe I take a letter for you and drop it in a mail box down the street, you say cheers mate and flick me a quarter ( if your over the pond). I come back and take your car, cos after all, I did you a favour, right? So that make it morally ok doesn't it!!!!

This is my definition of roleplaying in a nutshell. Any plausible action is roleplaying. Any implausible action is not roleplaying. And an action cannot be an "exploit" if it is roleplaying.

If I force an ordinarily lawful character to steal back training money I am committing an exploit. If I let an ordinarily unlawful character steal back training money I am not committing an exploit: I am roleplaying.