I'm SOOOOOOO glad you're considering reapplying!

I think Lorel's right--call them and ask. From what others have said, they're really good about answering questions. I don't think they see themselves as trying to keep kids out. They want to help.
Depending upon what they say--since they may say your previous letters of rec are fine!--I think I might suggest waiting until your DS has a new teacher/expert in his life to write the rec. If you can't wait until fall (since that's a gamble that the teacher will get him), maybe enroll him in a camp this summer? Find someone to babysit or work with him who has teaching experience? Something like that so that you have another voice with experience with kids.
I think you could add a letter of rec from your boyfriend, but I wouldn't rely upon that. If you need new letters, I'd treat his as an extra one. You can always add more, provided it all supports your DS's case.
If you have the scores, I'm not sure you need the video. (And if you don't I'm not sure it would help...) But if you've got the video, you might as well send it. They're not going to reject your DS because you sent them too much info! LOL!
I'd approach the whole app from a "more/and" stance. I wouldn't remove any examples or anecdotes, but I'd add the new ones. I'd just make sure to put the new ones at the top and the older examples below so that they see the new material first.
As for the RPG, my DS's obsession for the past year+ has been Transformers, and you can bet they heard all about that in our app.

I say put it down! RPGs are known for attracting HG+ kids, and they're full of math and history and mythology and literature and and and...So work it! Show them what he's doing with it! Use it for all it's worth!
I'm pulling for your DS! Here's hoping he gets the test scores that we know he's capable of getting so that the process is easy for you. That bubble is so hard on Mom.

And I want him in!!!
