Question #1
Can I order one with something cool like "Tin Cup" or "Cheeseburger?

No, the DMV does not do VANITY plates for Special license tags. The parrothead plates, just like college and other special plates, will begin with "JB 1", "JB 2", "JB etc".

Question #2
If I order a new plate in July, will I have to pay my property taxes?

A couple of factors affect it. One, plates won't be ready for several more months. Your check will be held until the first 400 are ordered, then followed by several weeks for production. (See the Process page).

As I understand it, this plate will follow the same guidelines as other specialty plates, so that if you have renewed your old plate, the new one will be prorated according to that previous one. Your taxes will be due according to your normal tax date.

I am sending the question to DMV for a clarification.

Thanks for asking.