"For a few of my buddies"? Okay.
I would think that if the plays aren't consistent dime plays or higher you're probably safe if he gets busted.
Before moving to Tennessee, I lived in Florida my whole life so I'll tell you what happened to me a while back.
About 16 years ago, my guy got busted. Turns out he was hanging around with the wrong guys as well as taking "action". Drugs, prostitution, I had no idea. I was just calling in my plays. Unfortunately, I was calling in most of my plays from work, which so happened to have a liquor license. FDLE came in and scared the crap out of me. Had me on tape calling in plays. The only time I've had my Miranda rights read to me. I about took a dump right there. They asked question after question about the "other guys" who I had no idea about. They kept pressing saying, "I was risking my liquor license if I didn't help them out". Finally they gave up and said they would get back with me later.
You know what really sucked? The guy who read me my rights was a golfing buddy who played in scrambles with us all the time. Scumbag knew all of us were calling in plays so I guess he wanted to get a feather in his cap by squealing to his superiors.
Anyways, turns out the 2 major players they were going after had a coke party and got some bad blow. They both freaking OD'd. Can you believe that? I get a letter from my attorney(who I hired immediately after I was questioned) saying FDLE was dropping the case because of their deaths. I still have that letter.
You probably didn't want to read all of this but what I'm trying to say is, if you get caught it's probably gonna be a misdemeanor(I know I spelled that wrong

) and you'll pay a fine. Now, if your "guy" is in to more than taking action, please be careful and whatever you do, DON'T CALL FROM WORK!
Man, the lessons you learn growing up.
nole