Long flights don't bother me because 1) the longest flights i do are really to florida so its just under 4 hours of flight time. But 2) I have my cell phone for skype and email , I have my 3DS (its paid for already ..... just want it to come out darn it ! ) for gaming and i have my zune hd for music and podcasts.
I keep my phone on me no matter what so its not adding ot my travel size , there are very few real games on andriod and while slightly more still not enough to keep me busy on a flight with the ipad so i'd bring my 3Ds also . My zune hd is the smallest thing i got so its not a big deal to bing with me. I can prob fit the 3DS , phone , tablet , zune hd and an extra battery or two for my tablet in the space of my old 15 inch laptop that i would travel with .
Okay...now with that pile of electronics you've got there I want you to do a carry-on-only trip around Asia (4 cities in South Korea, 6 in Japan and 8 in China) over two weeks with lots of trains and flights.
Packing light is nearly a religion for me. I own a PSP, DS, iPod Touch, a couple netbooks, etc., but taking all that crap is crazy. My phone does do Skype (over Wifi too since I won't pay roaming data in Asia), but not with video since Fring and Skype got mad at each other.
One key device I always take is my travel wireless router...hook it up to the in-room wired and both my phone and laptop (and wife's laptop if she's along) work without having to pay for multiple MAC addresses.