I once arbed a guy five times. No, I didn't know I could do it, so I wasn't looking to tell in advance.
Arb is for players with between three and five seasons of big league experience. The player was a 1st-round SP bust. I had him on a typical career path, put him in the starting rotation and by his third season he was getting shelled and no longer in the rotation. In his fourth season (first arb) I sent him down to AAA because I had the cap room to stash him there. Both that season and the next I kept him in AAA and brought him back up for September call-ups. Wasn't trying to do so, but it messed with his service time.
When he made it back to the majors to stay it was as an LR. As an experiment, I arbed him the third time to see what would happen. Didn't really care if I lost him, at that point. But then I checked the next season's arb report and there he was again. And the same the year after. And even after I arbed him the fifth time, he was willing to sign long term if I showed him the money. I didn't. Got a Type B for him.
Probably none of that would have been possible if he didn't have 98 Patience, though.