Basically, I’m semi-deaf, constant ringing in the ears, so pretty much anything and everything I use would be considered mid-range, but I want to get into the more technical side of audiophile equipment, but I have zero clue how, or what brands are considered a safe bet for a noob.
One interesting place to start might be to build a kit. Bottlehead is famous for their highly regarded OTL tube headphone amplifier kit, the Bottlehead Crack. It pairs superbly with high impedance headphones, the Sennheiser HD650’s being the classic example.
It’s a relatively simple assembly job that requires soldering skills, which can be learned while building the kit, and the ability to use a multi meter to read voltages and resistance. Also easy to learn. As well as care and patience. The instruction manual is excellent and their online community is active, friendly and helpful. They have talked thousands of folks through the process. It’s a great way to learn about audio.
This will expose you to a lot of different technical aspects of audio. And you will end up with one of the best headphone amplifiers available for under $1000k.