What kind of headphones do you use, and/or what codecs do they support?
I have Aptx low latency headphones I use primarily for TV, and use this monoprice and an old MPOW with AptX low latency (this one I think) and find they both work well. I found the low latency support was important for me on headphones and transmitter at the time, otherwise audio sync was too far off. Also supports AptX HD and AAC for higher quality when primarily listening, and ability to use optical in and bypass my TVs headphone jack was a nice feature on the Monoprice.
Avantree is another good brand I've used in the past. Mostly would recommend you find something with the codecs and inputs that are important to you.
Yeah, a (long) while back I did an ABX of known hard to encode samples and my regular music, found the setting I could no longer tell a difference, and added one more quality level to the encoding. I forget exactly what the level was, but around 192kb/s the best encoders for Vorbis and AAC were pushing transparency for me, and by going with 256 kbps VBR I was satisfied they were better than required and I could never tell the difference in my tests.
10 years later I can't really hear anything over 16Khz anymore, and pretty sure Vorbis/Opus/AAC at 256kb/s is fine for me despite the fact my equipment is a bit better than what I had at the time... I still have FLAC locally just because disk space is so cheap (have over 30TB of disk), but streaming spotify at Very high (320kbps Vorbis) gives me no pause, and high is probably fine for most listening environments/gear. Compression is a solved problem, and if you want better quality, you need to find better masters. Most high quality streaming services do in fact start from better masters when available, but then try to claim the difference is their compression/bitrate/sample rate/bitdepth, which is just bollocks.