I don't want to answer for 180toAJ either... but I did a BUNCH when I was on the ER. Most of the ER charters were a mix of military, NBA, MLB and NHL. Flying can be decent, food is good (typically). Occasionally swag comes your way. Sometimes its places you've been a million times. Sometimes it's different and unique stuff. Once spent a week flying around western Canada for some NHL teams, that was cool.

The charter coordinators are great and are the unsung heroes of the operation. They are the gate agent, ALA, ops and have some limited mx abilities. They get some extra training on aircraft ground systems and will typically wake the plane up and put it to bed for you. I had one go as far as get the ball rolling on a maintenance concern several hours before we even reported to the aircraft. The charter coordinators and FAs handle most of the logistics and passenger interaction. If the FAs need anything, they typically bother the coordinator whose job it is to fix it.

The only real challenges I encountered were operating in and out of FBOs and smaller fields, sometimes the hours are odd/backside of the clock deals and limited support capabilities for Mx or IROPS.

One tip I picked up was "let go of the schedule". Some guys have a hard time letting go of the schedule; but once you show up at the jet, you are on the team's time and team's dime. Don't ever make the team wait on you (if you can avoid it), but if you're waiting on the team then sit back, have another coffee and relax. Games get delayed, over time happens, media obligations go long. Your job is to be safe and legal, the schedule is up to the team. If you're running into a duty time limit, communicate that to the coordinator and they will figure it out/light the appropriate fires.

That was my experience. ymmv.