Steve
Mostly Harmless
This experience will help you be a better coach and a well rounded martial artist, but you just can't teach experience. If the goal is to build the same breadth of experience, the best thing the coach can do is expose the student to as many of those same experiences as possible.I've been fortunate enough to have the experience of grappling and/or sparring with wrestlers, judoka, jiu-jiteiros, capoeristas, karateka, wing chunners, boxers, samboists, MMA fighters, nak muay, aikidoka, power lifters, football players, completely untrained people, and many more.
And also, "working out with" someone isn't going to be of much benefit, unless it's relatively similar to skills already developed. What I mean is, rolling with a power lifter or an untrained football player isn't the same as fighting them or competing against them or arresting them.