In ear? vs. On/over ear? Your experience

I've had 3 pairs of around ear phones and the most comfortable pair of those was from bose. Pretty good, but an issue for me is that the ears can heat up over time.  It can get rather warm.

I had a pair of in ears from Bose as well, their top of the line sports model from about 2012.  The sound just wasn't as good.  For me the best audio quality and still cool option was an on ear pair from Grado.  Though much cheaper it rivalled the sound from a pair of well respected Nad HP50 at about 1/2 the price, the SR125e.  The Grados are also open backed, which may help things not to warm up as much.

None of the pairs I've had would retail over $300, so maybe beyond that level things improve.  I would imagine that in ear models have come a long way since 2012, the industry has really been growing.

If you have 300$ or so to spend for in ears.....check the reviews for the Blessing 2.....you'll have to wait for about 6 months after ordering.

Questions:
1...Yes..
2..No soundstage or imaging..
3.No...

There's no wrong choice, but if you value battery life and portability, on-ear headphones are probably the better choice. If you want slightly better audio quality, active noise cancellation, and don't mind heavier headphones, you should get an over-ear pair.