Nah, just like many other countries, the Bush administration and Chavez administration may have hated the hell out of each other, but that doesn't necessarily mean the people hate the people. I have a couple friends that have been down there for the same study program I'm going on and they rave about the experience.

As far as road and riding conditions, people do it all the time so I'm not altogether too worried, just gotta ride safe and steady. That being said, May is the start of the rainy season I found this thread on ADVRider:
Central America weather/rainy season - ADVrider
This guy put together a pretty good website in preparing himself for his trip this summer, rain and climate tables along with POI's for bikers. I'm going to keep my eye on it as it progresses. I was thinking of doing something similar, but no need to recreate the wheel.

For flying into Caracas, well, I haven't actually seen anyone who has done it myself, but someone suggested it to me as a possibility, so in another few weeks or so I'll track down the airline and call/email them and inquire about flying into Caracas. But where I'm going, Merida, it's pretty much equidistant whereever I fly in to 350miles from Caracas, 360 from Bagota, 400 from Medelin. So we'll see what happens to be more convenient. All things equal I'd take the flight to Cara, but if it was to add another day or two I'd might as well fly into Columbia. I'm not put off by either as everyone I've heard from has loved their experiences in both places, with most people saying Columbia was the best country of their entire trip.
Here's a thread from a Venezuelan that rode into Columbia, lots of beautiful pics...
11 Days Through Colombia - ADVrider