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I'm trying to make my mastering easier so I need to emulate how my master would sound on a pair of headphones, radio stereo cables, etc.

Is there a VST that shows me what certain analog output filters would do to my mix? Otherwise I have to test my mix manually on all the possible analog outputs that I have and it's very annoying.

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Checking a mix on as many different systems as you can access is a good way of discovering the deficiencies of your mix room & learning how to compensate for them.

Fixing the mix room EQ curves is a possibility - there are relatively cheap solutions such as ARC System 2 (Advanced Room Correction)

[Edit] I just noticed the ARC 2 has some presets included that may do just what you want...

New "Virtual Monitoring" feature mimics the sound of various listening devices like popular studio monitors, car systems, boom boxes, etc. allowing to the test of how mixes translate on different systems

otherwise...
Emulating all those possible playback environments is possible, but not easy & not cheap. Altiverb is capable of doing that, but the results can only be as good as your sampling method. It uses a method of modelling environments called Impulse Response [IR]

If you are modelling entirely in the digital domain, amps, processors etc rather than modelling speakers/room environments, then it can be done with simple audio spikes; but once you are trying to model the final speaker output, room acoustics etc, you then get into very expensive microphone/speaker territory, to make the resultant IRs worth the effort.

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There are a few speaker/headphone emulations I can think of off the top of my head. DeeMonitor http://www.musicradar.com/news/tech/free-vst-au-mix-checker-deemonitor-638156 is free with Computer Music and there are speaker and headphone emulations and calibrations from Sonarworks http://www.sonarworks.com/. iZotope https://www.izotope.com/ products have mix and mastering presets to deal with things like laptop speakers and other situations.

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