This is how I would go about it, and will hopefully fix your problem.
The M-Audio interface is 4x4, and that isn't always counting the headphone out (depends on make).
So in theory you should have enough ins/outs to make this work properly.
One of the inputs will be used for the mic, that's a given. You should be hooking up your monitors with the TRS balanced outputs. The Fast Track sheet tells me it has 4 unbalanced RCA outputs, but since you're already using 2 of the 4 total outputs, that only leaves you with 2 RCA.
So the cheap method would be to get a 2x Male RCA -> Female TRS adapter and plug that into the RCA outputs (3 and 4 most likely). Then plug a pair of headphones into the female TRS jack. From there it's easy. Say output 1-2 are your monitors, so you just assign that inside your DAW. Then make a stereo AUX channel and give it outputs 3-4 (the RCA outputs). This is your monitor channel. Anything you send to that AUX channel will be sent to the headphones of the vocalist in the booth.
You pretty much always send monitoring during recording via auxes, so this is a good habit to get into. Since it's independent from the main outputs you can adjust the aux all you want. Very indispensable as there is a difference between a good overall mix and a good monitor mix.
The not-cheap option would be to go for a different interface. It's quite silly really as 4x4 is all you need, but RCA isn't super dependable, especially if you have to run a long cord to a booth for instance. Expect pops and crackles if the connection isn't tight (loose connectors anyone?). So consider how many ins/outs you absolutely need and try and find an interface with that amount of balanced connections. Also throw in a small personal mixer to make your life easier. For example
this one or
this one (cheapo options). The musician can adjust his/her monitor volume themselves then.
In any case, never run audio straight out of your computer ports (the D/A convertors are crap), and try avoiding using the headphone output unless it's for a reference check on your own headphones (or you don't have monitors). Hope this sorts things out for you.
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