Well, the diamond level seems to include 4 nights at a Hilton. That must be worth at least half of the extra $1000 you pay for it.
None of the levels seem worth the upgrade. If you go from level 1 to 2, you pay $125 instead of $65 and get a poster and an option to buy a T-shirt. That seems exactly the sort of thing Chris would be dumb enough to fall for. The upper levels may be too rich for his blood, but he can probably scrape together $125 almost as easily as $65, and we know he loves poorly valued upgrades.
Or he might spend $250. That seems to be the first VIP/sponsor level, where you start getting special badges and recognition. Seems right up his alley, and $250 is not out of the realm of possibility for him.
To be fair, conventions like this are difficult to price. They are expensive to put on. You have a large amount of venue space for a long time, plus a whole bunch of equipment and logistical support to pay for. You want decent sized crowds, so you need your basic price to not be a barrier to poorer fans, and hopefully entice some locals to stick their heads and look around. You can have more expensive packages, but you have to be careful, because if the place is full of VIP only events it gives it a really bad vibe for the people who forked over the basic price. The best way of squaring that circle is by having corporate sponsorship, and I am not sure how much of that is floating out there for dumb shit like Bronycon. So you are left with the next best option, which seems to be the one they went with. Have a bunch of overpriced "exclusive" knickknacks and minor perks, and hope that superfans with money to burn will get sucked in.