Best on/over Ear Headphones for Everyday Use and Sound Quality Under $200?

I would send you in the direction of the Sennheiser HD25SP or the HD25 1 mk2...the HD25 1 mk2 is more expensive...it's worth it though. I liked the Sol Master tracks...it might not suit you, sounds good and its almost indestructible - I reckon its worth considering. The sound of the HD25 1 Mk2 is what you are looking for...it's a great can...I have the aluminium version.

1. Bose or Klipsch In Ear headphones? Whats your opinion?

I owned both Klipsch S4i and Bose MIE2i. First I came from really enjoying the Klipsche S4i, which sounded really loud and fantastic! However, after extended periods of time, the in-ears felt a bit uncomfortable. Also the build quality lacked any longevity beyond 6-8 months. I had it for 1.5 years before it was broken. I was being very resistent to Bose headphones at first because many reviews stated it was overpiced. But I had to find a replecement for my Kilpsch S4i so finally I did give Bose a try. Well...much to my surprise...they sounded fantastic too! They were not as loud as the Klipsch, but the highs, lows and mids are well balanced, and should suit any listener ranging from all tastes, across the board. I miss the bass on Kilpsch, though. But with Bose, you will hear the mids and highs are just right for a very comfortable listen. Also they feel quit comfortable in your ears, regardless of what they may look like. you can barely feel them. I could wear them all night without any complains. As with Klipsch, it hurts my ears a little if I wear them all night. My only complaint would be that Bose do not provide a noise canceling seal, so you tend to pick up outside noise, which can be a bummer sometimes. However the acoustics are so good on these, that they tend to keep the music as the majority in your ear, so it's not too bad. It would be nice to have a noise canceling version of these, someday. But if you like to work out on the street, noice cancelling is definitely not safe to wear, so better go with Bose if you need a bit of noise outside coming in. But overall...I HIGHLY recommend these two, depends on which you prefer and most suitable to your needs.

2. Among on ear and over ear headphones which one is more comfortable and best fit for ear?

I vote for circum-aural (around the ear) headphones as the most comfortable, since they do not squish my external ears (pinnae) like supra-aural (sitting ON the ear) models do. You get a better seal against the skull rather than the ear, since ears are such different shapes and sizes. My favorite long-term phones, used back when I was broadcasting my radio shows, were the AKG K240s, and guests almost always found them very comfortable without any adjustment, and I still find them very comfortable years later, despite the years of progress in headphone design. This comfort (along with the neutral sound) may explain why this model has been in production for over thirty years, with just a few upgrades along the way (like replaceable cables).Among on ear and over ear headphones which one is more comfortable and best fit for ear?

3. The Best In-Ear Headphones under $150?

First off you should rule out Monster as they are known to make overpriced and mediocre products. As for Bose meh.... they are only okay. Now on the other hand you mentioned Harmon/kardon and that would be a great choice! they make very good audio equipment. Shure and Bowers are fantastic brands as well! I would choose between those three.

It might not be the headphones - try them in more than one device to see if that's in fact the problem before doing anything else. If they are the culprit, and pressing firmly on the jack helps, it may just be a bad connection. In that case, your best and quickest option would be to just purchase a new tip, cut off the old one, and solder on a new connection.

5. What are the best sounding wireless over-ear headphones for under $500?

Can't go wrong with Sony WH-1000xm2 or newer xm3. Excellent headphones with great noise cancelling and comfort. Prefer these over Bose, Beats, AKG's, Sennheisers or Bowers & Wilkins. Sony's MDR-XB950N1 EXTRA BASS Wireless Noise-Canceling Headphones are an excellent choice as well if you like bass. The bass sounds really low and punchy. All of these headphones are well below your budget in the $180-$350 range.What are the best sounding wireless over-ear headphones for under $500?.