I'll go on another tack, you could consider a Skywatcher 70 x 500 AZ3 from Andrews.
http://www.andrewscom.com.au/site-section-10.htm
I use one as a grab and go for a quick look if I don't have time to set up and cool the reflectors and I find it fun. It will not challenge the bigger scopes at all but it is very effective on the moon, planets (although they are quite small), the brighter nebule, double stars and clusters.
Really easy to use and learn his way around the sky. He would also need a red torch to preserve his night vision and a plansiphere (I use the large Chandler one).
As mentioned before nothing replaces a dark sky so get in touch with the local astro society and attend their new moon nights. Membership in the local astro society would be a great pressie as well as a nice set of larger binos, red torch and planisphere if the scope and accessories are out of budget. I used a pair of 7x50 binos for years before getting my first scope.
Then start saving for next Christmas for the 8" dob
