I'd get the Wildcat, if that's the boat you want. If you know the basics of sailing, you'll be OK. The major difference between the Wildcat and a more sedate cat (like my Getaway) is you will get better at righting it after a capsize from all the practice you'll get!
I started with a H-17, had a few monohulls, have sailed boats as varied as Lasers to Interlakens to scows to J boats and a 34' Mull racer in a sailing club, and now have a Getaway. What you are going to do with the boat should determine which boat you get. Heck, a monohull (shudder!) may be the best boat for you!
As far as rigging time, that depends on how much you have to tear it down to trailer it. I take off the rudders and bob from my Getaway to trailer it, but I have to drive an hour on the highway to my favorite lake. If it was just up the road I would leave them on. I have a motor I put on it, and I almost always rig the spinnaker. Takes my wife and me about 1/2 hour to rig it, including the beer cooler...
But your intended use should dictate the boat. I bought my H-17 from a Hobie dealer who told me it was a good family boat. As you may know, the H-17 is a solo racer. It was too small from the beginning. But when I went out alone on it, it was a blast. It was just ok with my wife or a kid or two.
So, are you mostly sailing alone? 16, Wave or T2. With a bunch of friends? Getaway. Mostly with one or 2 other people (and you want to go as fast as you can)? Wildcat.
This is all opinion, of course.
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