While your system would be fun to build and operate I find that its a lot quicker to just haul them up. If you use a "nose-cone" or just make sure that the cable is hooked to the bottom side of the log it won't really tear up the terrain if you watch your pulls, as opposed to just trying to muscle them up with the tractor.
200 ft of rope is a long run to buy and handle but with the skyline you will be dealing with at least twice that amount of cable plus the drag rope.
If you have another body to drive the tractor then I'd also invest in a set of radios, preferably with a "hands free" feature.
My land is also mostly up and down and I limit my pulls to 100' or so. Since I work alone I use a $400 4ton electric winch on the back of the tractor with a wireless controller. I drag the cable down the hill, hook up, then return to the winch to engage the clutch, climb back down to where I can see the log and hit the remote for the winch. If the log hangs up I release tension and fasten a small (light) snatch block to a tree to guide the cable and log around the hang-up.
I skidded out about 6 bush cords last year, mostly dead oak and other hardwood in the 4-12" diameter range, seldom having to cut to length until it was up at a landing where I loaded unto a trailer/log hauler that I've built.