I vote for leaving it alone. I don't think the '08 tail section looks better without it. If the tail section was more aggressive looking and more angular, I'd say remove it.
It doesn't weigh much, doesn't cause any drag, and keeps a lot of crap off the rear end when riding through wet weather, and gives you a place to hang your license plate.
I experienced the same problem as SCAR did with my Pit Bull rear stand. I resolved the issue by rolling the bike's rear wheel onto two staggered pieces of 2X4 first, and then lifting with the rear stand. This extra boost in rear height prevents the interference from the tail piece to the stand's handle.
You won't need a second set of hands, but some finesse is necessary. I started by keeping another 2X4 scrap under the kickstand, as well as under the rear wheel to allow the bike to support itself while I positioned the stand. After a couple of uses, I have it down to a science, and don't need the kickstand support. Another option would be the Pit Bull forward levered lift, but personally, I like the rear lever style.