The car will do fine on any trip you take in it, well as long as you keep it out of the snow.
-For long trips, if in a hot enviornment it could get warm in the car (If you get the GTS).
-RT/10, at least the early ones are not for driving in the rain, top/side curtains leak.
-Aftermarket parts are expensive, actually all of them are, well expect the oil filter
-Not easy to get in and out of (GTS worse), watch out if the side sill if it is hot.
-Since you are looking at GEN II I would stay clear of 00-02 if possible, that is when they went to cast internals, look for a 96-99.
-The looks of a GEN II, best looking performancecar built in the 90s, of course that is opinion.
-Uniqueness, you are not going to see many on the road with you, where as with a Vette your hand will get tired of waving at fellow owners.
-Depriciation is done on GEN Is and some GEN IIs, you will get your $$ back when you sell it unless you do something stupid.
-The looks and questions you get. After a couple of years it will get to be a joke, but on a good day still entertains me. I have a couple good stories!!
If you have particular year in mind I may be able to add more info.