#2
If you're carrying a laptop, then what exactly is the point of putting all that onto a flash drive?
#4
Instead of that, use the suite from portableapps.com , it works amazingly - and it's free!

The forum there is very helpful, and can give you a hand getting things working, not that it is complex at all.

There is an emphasis on free open source applications like Firefox, Gaim, Gimp etc, so everything is free and simple.
Every inside out badger has a silver lining.