Sounds like a pain in the ass, hope you put enough money on it to justify the time, or are working for a good hourly rate.
More important than the source of your pull, is your lead angle. The closer to 90 degrees, the better. At 90 degrees, 100% of the effort is pulling sideways. As you get close to 0 degrees, the effort approaches 0%. Use slope to your advantage where available (always pull form the up side) and avoid at all costs pulling form the low side. You can do some tricky pulling situations if you have enough ropes and rigging - you can set redirects high in other trees lower down and then pull form the up side. But it sounds like you're probably not geared up for this.
Keep your lead angle as close to sideways as possible (ie - get far far away) and even a small pulling source like an ATV or a human can make a significant difference. I'm Ass-you-ming you have some way of setting your high line like a big shot and throw lines, or can spike. While I'm assuming I'll take it a step further and guess that you have also plenty of wedges and know how to fall. Might be worth getting a climber in for the day. Might cost less than a winch and give you a better result.
If you're pulling uphill and have a big enough winch at the top of the hill (usually hydraulic on a big truck) then you can set a pseudo highline by rigging a rope to the top of the tallest tree you can find near your lift, then taking the line down to your lift target. Hook your whinch line with a pulley onto the rope, and the lead angle will bisect the two, giving you free lift and keeping the logs from snagging on the way up. You get a mechanical disadvantage of 1:2, but it usually works out to be worthwhile. Be sure the highline tree is stout, or backbrace it. Of course, if you have a tall tree at the top of the hill you can rig a better high line, but i find the former situation occurs more often than the latter in residential scenarios.
Shaun