What about upgrades for Apple products, such as my Late 2011 15" MacBook Pro?
I would buy two 512GB SSD's once the price comes down, an Optibay enclosure, 16GB of 1333Mhz DDR3 RAM, and a large external HD (probably 2TB) for backing up all my data. I would set the drives in my computer up in a RAID setup for super fast speeds. I would also buy an Apple Thunderbolt Display and an iPad.
This should (if I buy once prices come down) come out to around $2300 USD, the price limit set in the OP. I would have a stellar at-home setup with an amazingly fast laptop with an incredible display, and I would have an iPad for on-the-go productivity, web browsing, entertainment, and school work.
Sweet....
Edit: Does Apple stock count? I'd be in for $2350 USD worth of stock actually.