You are correct there, that your second event will be the standard $50. Rerolling will be no problem, just see any of the New Player marshals prior to the event and we can work with you. If you send me a message with your e-mail, I have a Google Drive doc of the new character builder worksheet that we can work on and you can print out ahead of time. You can bring that to an event, have it double checked by a marshal on site, and you're golden.
As far as the Spy thing goes, a lot of people pick up additional classes to go along with it, so they don't have to have that same awkward conversation you are suggesting. If you need any additional help, feel free to PM me.
Elias Ashby
Proprietor of the Ashby Family General Store
Lord Templar Rayven Nightwing of the Order of Holy Light
(OOG - Matt D. - Photographer)