cforst,
IFR in a small airplane can get you into just as much trouble--an IFR trip like that in a single-engine airplane with ice and/or thunderstorms might be above my skill level as a 500+ hour CFII. An instrument rating does not make you or your airplane invincible. Even in my limited experience, I've seen many pilots with misconceptions of what they or their airplanes can do. For example, I've seen newly rated instrument pilots that think that they can tackle the same weather as airliners do. Also, I've seen ex airline guys that think that GA planes can do everything that their airliners could. It just doesn't work that way, that's all.
I think it'd be a fun challenge to try it VFR though, and you can always get flight following if you worried about always having ATC contact. As Buck wrote in Weather Flying, just make sure that you are a "weather skeptic" and always have an alternate plan of action.
Edit: I don't want to come across as not being in favor of getting an instrument rating. Far from it, in fact. Instrument flying is what I find to be the most satisfying and enjoyable, and any additional experience is beneficial. I'm just saying that in a GA single on a trip like that, I think that it would be much easier to manage the risks involved while flying under good (i.e. not night, not marginal) VFR restrictions.
-Goose