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

I bought a pair of relatively inexpensive NuForce IEMs after reading some favorable reviews.  I bought them for traveling.  

Overall, I am not a big fan of IEMs.  Mine sound fine, but I just can't get comfortable with them inserted into my ear.  I replaced the OEM tips with Comply tips, which I find a bit more comfortable.  However, I really prefer the comfort of a regular headphone, either on-ear or over-ear, for longer listening sessions.

Naturally, this is a matter of personal preference.  I wonder how custom-fit IEMs would feel, but I really don't use IEMs that frequently to make such an investment.

For me, nothing beats the small size and convenience of IEMs. My RHA 750 and Shure 535 sound great. Thinking about some customs....

The often overlooked disadvantage, to me, is that if you're interrupted and have to remove one of them to hear someone,  it takes a few seconds to replace them in the ear afterwards.  As opposed to on-ear or over-ear headphones that are easily placed over the ears. 

Also, people don't always notice the IEMs and will speak without realizing you can't hear them. With headphones, they will wait until you remove them. 

For me over ear always sounds better than in ear.

I went extreme TOTL for in ear set up and just was not satisfied due to limitations of IEMS. Just my opinion but some people love in ears.

IEMs did improve a lot over the years.

I had the u18t, sp2000, and a pw1950 cable. That retails for 7000 together roughly and it didn’t do it for me.

General rule is speakers over headphones over IEMS, but everyone has their own preferences.

I find over the ear better because they're just more comfortable, from my experience at least. I do wear in-ear ones, but only when I swim, got my hands on some waterproof headphones that are quite ok, some Platronics that I found reviewed online. If you are keen on in-ear, do some research first, or else you'll end up with pool sound quality.

Don't expect the same quality as with over the ear though, and from my point of view at least, don't expect the same comfort in the long run. But it's best to have some in-ear headphones too cause you never know when you'll need them, especially if you go for waterproof ones to wear them when you work out or do other activities that involve sweat and water. Here are some models worth checking out, maybe it helps:
https://popular.reviews/waterproof-headphones/

In ear monitors can sound as good as around the ear ones....you just have to pick the right pair.   In ears should be auditioned for your own comfort.....larger, smaller....to fit.

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.