2) Why exactly have you been pondering over it for so long? The cost of trying is next to zero. At worst, you'll end up with an unusable test machine, give up, and try something else. Simply going ahead and trying is probably better use of your time and energy than pondering for a long time and looking for advice as to whether you should try.
Why not ? A lot of us like to learn just for the sake of learning. I say becoming a Linux power user is a worthy goal in itself.
I agree with your point 2), it's fair easier to dive in and try it, rather than ask in forums if you should do it. It's not like it's going to cost you anything. Just download Virtual Box and do it.
2) It's mainly because I'm halfway through the alpha-launch of my web-startup, and have a little time to spare, which I want to use productively. I haven't been 'actively wasting time pondering over it' , it's more like 'been at the back of my mind' sort of a thing.
//edited: making my point more clear.
Try living out of a TTY for about a month. You will come out with rustic beard, red eyes and a triumphant smile. No Gnome or gdm, screen to take care of your "windows", mpd (ncmpc) to play your music, elinks to browse the web, surfraw to search, vi to edit your files, irssi for irc, bitlbee for msn etc. Control your daemons with rc.conf and begin your journey :)