I was watching a chopper hover at low altitude one day and visually watching the pilot watch me watch him

It made me think about how different the two classes of airmen really are and how little the two types of flying have in common.
Are there any airplane/or chopper guys who crossed the line?
What was that experience like? and does it actually take longer for a pilot to crossover than for a complete novice?
What were the biggest difficulties you had in training?
What airplane habits are especially hazardous in a chopper?
How scary or difficult are autorotations?
What skills do tranlate if any?what's the very first time at the controls like?
Lastly, what is used a typical trainer for IFR and VFR operations?
Sorry, for so many questions, but I'd love to hear anyone's stories and experiences I'm sure a few real life accounts would adress my questions anyhow and I'm a sucker for good flying tales.