Hello, this is my first post on the forum. I’m happy to have found such an amazing group of thoughtful people all interested in audio and headphones! I am new to the mid to high-end headphone arena; previously I have owned Sennheiser HD 280s, and I currently have a pair of Sony MDR-1RBTs (the Bluetooth version of the MDR-1Rs). I have liked the way both sound, but my main problem with both sets is that I have a big head (7 3/4 hat size) and they feel like squeezing after 60-90 minutes no matter how I adjust them. I also don’t know what I am missing, as I’ve never owned better headphones than these, and I’m interested to find out what is possible. I am looking for a headphone and amp setup for preferably under $500 total. I’m willing to try used. Type: circumaural, open or closed, leaning toward open for more comfort. Sound: I listen to all types of music from classical, metal, and country, to hip hop and EDM. The music where I really get that frisson sensation is mostly cello and violin, or female vocals. I do enjoy good sub-bass response but would prefer a neutral response. I would also use them for watching movies and Netflix. Source: Currently Spotify on an iPhone, iPad, or laptop. I may try Qobuz soon. However, I also need the capability for an analog connection at work, so any DAC/amp combo must also have an analog in. I don’t need higher than 16 bit with 44.1/48khz, and I’m more than willing to use Apple lightning and USB-C to 3.5mm DACs, as I’ve heard good things about them. It would be good if the headphones could sound at least decent without an amp, but I’m flexible. Comfort is my #1 priority. Unfortunately, due to my location it’s unlikely that I’d be able to try on any but the most mass-market headphones prior to buying. That being said, the Sony MDR-1RBTs felt great for the first hour, so trying on in a store might not help. I’ve looked at the Hifiman HE4XX and several Sennheiser models, including the HD 6XX, HD 58X, and HD 650s. I’m willing to entertain any ideas. Thank you guys for any suggestions you can provide!