my goals are really just a discussion on what people do when they need to listen via headphones. i'll probably end up picking up a really old pod or something. dont want to drop 2k on a setup like yours. but really this thread isnt about what i may do. i want to know what people who use headphones to play do. so your reply was exaclty what im looking for.
Grado headphonmes are amazing. Alessandro has some Grados that are made to his specs and are very nice. There are many headphone amps that range from 100.00, to many thousands. depends on your budget. I have mine made by Audio by Van Alstyne, and costs some bills, but worth it. Research the internet. I prefer tubes, and seem to warm it up the most. You can find some real bargains.
I use a Jamvox which has a cool computer interface with amps, cabs, pedals you can add and subtract modify to your hearts delight. It has drum tracks, you can download your Itune library to jam along, cancel out guitar parts and jam with your favorites. It also records them too. Cost like $250. It's the bomb for the price.