Hey! I am actually no longer on the road. I had a chance to try out a full time regular dealing job so that's what I'm doing now.
A few changes I can think of since the original post:
1) The WSOP now hires around 1000 dealers, which means each dealer they do hire tends to work more hours. You should be able to make $8k-$12k over the Summer, working 6-7 days a week. They schedule you for 6 days and there are often signup sheets where you can volunteer to come in for a 7th.
2) They no longer hire chip runners, so there are fewer jobs you can get that don't require taking a class. They do still need cashiers and clerks, just not as many as before.
3) The big tax law that went into effect for 2018 makes it so traveling expenses are no longer deductible.
#3 will not impact you a whole lot if you only do a few jobs a year and are in a low tax bracket. Those of us who were traveling year round were affected quite a bit, which is one reason some of us decided to get off the road. I often miss the road and I may go back when the cabin fever gets to be too much.
Summer in Vegas is the easiest way to get your first job and gain some experience, but there is work year round other than December, which can be hard to find spots.
Another opportunity I didn't know much about when I posted was massage therapists. Players like to get massages while they play and therapists are brought in for this. You do need to be trained and licensed. You work for tips plus I assume some base rate. I don't know what pay is like, I'm sure it varies. It's mostly women who do this, though there are a few men at the WSOP.
https://www.professionalmassageinc.com/careers
http://atouchofluck.com/careers/
You can always pop by a tournament near you to check it out. Look for bored dealers or therapists standing around and talk to them, or just soak up the atmosphere for a bit and see if it looks appealing.
https://www.cardplayer.com/poker-tournaments/