Hi Mandi
Yup, 8" dob is the way to go.
Collapsible version at
Andrews is $449 plus $50 shipping to you, therefore $499 delivered.
Bargain. Less than $500 large. Might be a good idea to get him a laser collimator too for $59, planisphere for $15 and an astronomy 2011 magazine for $10. The collimator is an essential tool to help him align the mirrors to perfection and makes everything sparkle. The mag and the planisphere will be all he needs to use for now to find his way around the sky. A $10 red light torch "swlight" wouldnt go astray to be able to use the books in the dark and keep your eyes dark adapted.
So, all up I suggest $449, $50 delivery, $59, $15, $10 and $10 = $593
Yes, it all adds up but this is a great beginners package and the best place to start. AND its still $7 within your budget.
Cannot go wrong with this. Telescope comes with a 6 year warranty too which is great peace of mind.
Cheers
Chris