Looking for help selecting a IEM and/or wireless with good microphone

[neilmon2]

Thank you for taking the time to read and help me with my journey. I know all of you are busy and I will make it a priority to respond to every comment.

Budget - $500

Source/Amp - What are you plugging the headphones into?

• Google Pixel 3
• Apple Macbook Pro
  

How the gear will be used

• Listening to music while and phone calls while traveling (planes, airports, coffee shops)
• Used to get people to leave me along
• Secondary use for something portable would be to wear it around my house. I like to listen to music while cleaning and doing dishes. My wife and kids don't always want to hear it.
• Possible working out by I have a pair an OLD pair of jaybirds bluetooths which I currently use. They are very uncomfortable.
  

Preferred tonal balance - Probably looking for something more balanced. I do enjoy hearing the detail of an acoustic so something with a clearer high over a big bass is probably preferable. Also, I've found that a big bass sound makes calls with clients harder to hear if they don't speak very clearly.

Preferred music genre(s)

• Signer/Songwriter mostly acoustic.
• Rock - Alternative/Oldies
• Jazz
• Audio Books
• Phone Calls
• Some some occasions top 40 pop
  

Past gear experience

• Bose QC25: These have worked ok as noise canceling. I've always been told the sound quality is not good, but they seem ok to me. As I've gotten older, I'm less picky. The main issue is with comfort. I wear glasses and these are not comfortable over a period of time. Plus it's tough to sleep with them on a plane. My experience with phone calls has not been great either. I've been told I was hard to hear.
• Sennheiser CX 1.00 (https://drop.com/buy/massdrop-blue-box-sennheiser-exclusive-grab-bag): I generally like these. They are light and comfortable. The mic seems to work pretty well. Sometimes I will need to bring the mic to my mouth, but that's not a huge deal-breaker. The sound has been acceptable. My biggest problem I have is with the cord. It's very flimsy, and currently, the metal is exposed on several parts. The issues with the cord were caused by me stuffing it into a bag or my pocket very haphazardly. A stronger cord and/or an easy place to store the headphones is essential.
• Beyerdynamic DT 880 Premium Edition 250: These are my home office headphones. They are amazing. So comfortable, I can wear them all day even with my glasses. The sound quality is outstanding to me. It's currently using a Fiio olympus 2 but I'm moving to a Schiit Modi/Vali stack after reading reviews over at r/headphones.
• sennheiser office runner: I use this for phone calls at home. While I love the comfort and wireless ability. I've found it difficult to hear people at times. Mostly with low voices.
• OLD (4 years) Jaybird bluetooth: These are not great. Very uncomfortable, the sound quality isn't good and the mic is terrible.

I've thought about some of the true wireless headsets like sony WF-1000Xm3, but I'm apprehensive about the microphone. I read on another review about detachable wires and that sound very interesting to me but searching around seemed very overwhelming. I was leaning toward getting a good wireless for portability then a wired for calls and as a backup. For my budget, I feel I could good 2 sets of good headphones.

After writing this post, I've extracted a hit list of what I think is important.

• Portability
• Either wireless or a strong cord. I'm not careful with stuffing it in my pocket or my computer bag.
• Strong microphone for calls with clients while in public places
• Crisp/Clear sound.
• Comfort, can I sleep on them in a plane
• Prefer IEM. I've never used a neckband but I'm very open to it.
• I'm open to multiple sets if they are both portable.
• Both of the devices used will have UCB-C but I have no problem utilizing an adapter.