I would go with the 16 footer since its in better shape, $200 less and the trailer looks like its made for the boat while the other trailer looks homemade or thrown together.
Do you need the extra 2'? That's what you need to decide on.
The extra 2' will give you more elbow room, storage, and a better riding boat if the lake gets rough.
The 16' will be easier to maneuver on the water and get blown around a little less. Fit easier in your garage if you wanted to put it in there.
Oh Yeah.....To answer your topic title...NO I wouldn't give that much money for either one of those motorless boats. Somebody would have a hard time getting $1000 for either one of those boats around my neck of the woods. Occasionally I see fully rigged Basstrackers for $2K or less. Last year I sold an older 17' Basstracker with a nice Minn Kota Maxxum trolling motor with an older 85hp Mercury (ran but needed worked on) for $1200. I paid $1100 for it and fished out of it 4-5 years.
Those boats your looking at could be fairly priced for your area. If I were you I would check all the Craigslists within a 5 hours drive from you and see whats out there. A 10 hour round trip is nothing compared to the amount of time your going to spend in whatever boat you decide to buy. If your near Florida or Texas check them out since they seem price their used boats cheaper.