I stand by not looting corpses either way. It is a fun restriction on gameplay to help you stick to the character. As for stealing from the trainers, I can see your argument for not pickpocketing the trainers, but I want to see my character become a Master thief.
At first you wouldn't be able to steal the gold every time but as you became a better thief you'd have a better chance of stealing everything back. A fun middle ground could be making it a rule that trainers who catch you x amount of times will refuse to train you from then on. Maybe take it further and by depositing a large some of gold in the trainers home, they would agree to start training you again.
I stand by not looting corpses either way. It is a fun restriction on gameplay to help you stick to the character. As for stealing from the trainers, I can see your argument for not pickpocketing the trainers, but I want to see my character become a Master thief.
At first you wouldn't be able to steal the gold every time but as you became a better thief you'd have a better chance of stealing everything back. A fun middle ground could be making it a rule that trainers who catch you x amount of times will refuse to train you from then on. Maybe take it further and by depositing a large some of gold in the trainers home, they would agree to start training you again.