If it was my money, I'd buy the Skeeter if I could talk them down some. It's a bigger boat, bigger motor (and that 01 Yamaha OX66 is a great motor by the way), tandem trailer, showroom condition and I'm guessing it has better electronics on it than the Ranger. (the Ranger electronics didn't look too promising).
Another thing to consider is that the economy is circling the drain and it's not a very good time to be selling a boat. Or a mtorcycle, or a house or .....well, you know. Unless your current boat is priced to sell quick, it may take a while for you to sell it. A trade in will probably not get you the full amount you want out of your boat but thats the quickest way to get rid of it and into something else.
It all comes down to which you will be most happy with. I would recommend doing the compression checks on both motors and test drive both before making your decision.
Good luck and be sure to post up some pics whenever you get the new one.