That you for your detailed response, much appreciated! And sorry for a late reply!
I’m aware that it might be difficult to give me any advice as I’m not someone who tested many headphones so I cannot really help by listing those I liked.
As for the headphones I use, it’s been more than 10 years now that I use a pair AKG K99. Those really are not high-end headphones by any means, they have flaws. But I like their overall sound characteristic. I had a chance to compare them with headphones few times more expensive and I still preferred how the K99 sounded. But it might be because I’m so used to them.
As for the IEMs, I’ve never really used them. That’s why is so hard for me to imagine how moderns IEMs compare to modern headphones. I once bought Snab OverTone EP-101M, but they were so uncomfortable for me (especially in bed) that I ended up not using them.
I’ve never heard neither Sundaras nor Shure’s IEMs. I picked those brands/models solely by watching and reading reviews.
In music that I listed to I mostly concentrate on the instrumental part. I like jazz, rock, metal (and also genres that combine jazz with heavy sounds - one would call “technical”), blues, classical music, audiotracks from movies/games etc. I rather don’t listen to pop, rap, hip-hop, techno etc.
Making calls is not that important, anything would be enough. But I like to listen to music in bed (Shure’s IEMs seem like they won’t push against my ear too much) and sometimes on the go. My primary use seems to match headphones more - sitting at my desk in a quite environment - it’s were I’d like most of my budget to go. But if I can get good sounding IEMs, then why not buying them instead and enjoy a good sound in every situation? What bogs me is that I don’t know what to expect from good IEMs as I never owned ones. How do they compare with headphones?
Thank you for all the recommendations. I’m still looking into the IEMs models you’ve listed. I must admit is a tougher nut to crack for me.
I did also consider (I still am) HiFiMAN Anandas and Focal Clear. Seems like if I decide to go for good headphones then picking the “right” model will be a blind shot - unless I find a way to listen to them before buying.
Thank you very much again!