That's a tough one! Option 1 would be nice, but you and your second person would have to take time off work, which could be a problem depending on where you work/if you have vaca time.
I have an iPad, iPhone and iPod but I could probably sell the ones I win, and I would love to have a Mac computer.
I'm sure I would have no problem spending $5,000 on sexy things.
Maybe I'd pick option 2, sell the stuff I already have/don't want and use the money to buy a new toy and/or a spa day