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Do you have a Mac? The GarageBand amp sims should be very decent if they're anything like the Logic ones, so you'd only need a pretty simple interface to plug into (they can be really cheap these days!) and you're away. Also quite nice if you plan to play along anything as what you hear then is de facto mixed with the track!
The problem I’ve found with using headphones plugged into an amp, or into the phones socket on an attenuator, is that the raw output from the power amp often sounds pretty unpleasant, without it running through a loudspeaker. The Waza Air as mentioned fixes that by simulating everything, including speakers. My solution was to use a cheap Mooer IR/cab simulator plugged in to the line out from my attenuator. Works beautifully, really natural sound.