if u want a good headset for life, waste rly money: take a Beyerdynamic DT 109.
u will have the football commenters style but its very nice to carry for hours.
They have some lightweight system too, maybe check how the tests are for that.
For indoor use i would personally tend to an open system, cause closed headfones make ur ears get "cheese layerd" like feet in hot weather.
sure u hear things from around but that can be nice too...
what belongs to the monitor: dunno.
samsung made the great crt syncmasters that were kewl for gamers. i think they make good quality, price is so-so
when i see how monitors grow atm, i personally would wait a jear...