I'm not so sure. These guys don't earn jack shit, even if they win small Futures/Challengers. Taxes, equipment, travel, etc.. adds up quickly. Forget about coaching at that level.
Not the right environment to go party with someone one night and then have to beat them the next day in order to put food on the table.
Keep in mind that at this level, tennis is fucking insanely hard. A few guys from my high school tried that level (they all played D1 at top schools, a few were top 20 USTA as juniors, one made top 3 ITF and was highly ranked within the college game) and none of them fared well.
These (challengers/futures level players) aren't some random scrubs - these are often times guys who either played top college ball, or guys who were top 100 ITF juniors (or top player in their country/region) who never had the game to get to the next level, or guys who were just not quite good enough to make top 100 ATP and need to grind every day to get auto entry to qualies at majors or ATP Masters events.