I mostly use an iPod touch 4th gen and a MacBook as sources (I'm aware they're not the top of the line and have a bad reputation) and I'm looking for advice as to what my approach should be to improve my listening experience. I'm starting to get into vinyl too (still a beginner) and I have an Audio Technica AT-LP60 turntable for that purpose. I was wondering if getting better headphones and an amp is worth it given my sources. Right now I have a pair of Grado SR-80i which to me are a little bright at times and after listening to music for a while they can be very uncomfortable and fatiguing, so I guess the Grado sound is not for me. For traveling purposes, I have a pair of TDK BA-200 IEMs that do their job well. I'm looking to upgrade my listening experience at home, so portability is not an issue and if the headphones are open/closed it's not a deciding factor. Ideally, I would prefer over-the-ear vs on-ear headphones for comfort.
The music I listen it's mostly rock and metal (80%) and some classical, jazz and electronic (20%). In terms of budget, if I could stay under $300 for headphones and amp (if needed) it would be great, but I'm willing to consider different options. If upgrading my set up at this point is not worth it, please let me know what your thoughts are.
Thanks for your assistance!