It sucks more for people who only can play at certain times of the day, and during those times the servers are down. Luckily for me I can play pretty much whenever, but still. (bragging) (but it's kinda sad to be unemployed)
Oh yeah, just wait another few years for the next DS. Then, while your at it, just wait a couple more months before you decide to get a new iPod. Hehe.
Seriously though, I'd say get the DSi. I don't play GBA games, and I honestly think that some of the better GBA/GB games will come out as DLC on the DSi store. If your strapped for cash, and do enjoy the GBA titles, the DSLite is cheaper and has the GBA slot. I really don't use the new features of the DSi.
I dont think Nintendo would do this. There might be a few game developers that decide to bring their games to Nintendos handheld, either through DSiWare or retail games, but not many. Especially game like Rolando, which I think are meant to be iPhone exclusives due to their "tilt" mechanics.