Joel, Oh to be 15 again! (that was almost 50 years ago) I've been pulling wood for over 40 years and rarely have any slip. A few points. Use a good alloy choker, the links are smaller and slip very easily to tighten. Have a slip hook on the chain, ones designed for logging have a C shape with a rather small opening to hook over the standing end of the chain. Don't bundle more than the chain can actually have each touched by the chain unless there are limb stubs or forks that will catch other logs/branches being pulled.
You show a 3 point hitch arch. Just back up over the pile, lower the arms and hook the chain as tight as it will easily go. Hook to the arch last lifting the chain to remove any slack. (The arch should have a grab hook to connect to). Raise the arms and drive. Sometimes if the starting load was spread you will raise to bunch,lower arms and re-tighten chain slack, raise again and drive. You must remember that with this type of arch you are pulling from above the drawbar so a rollover is very possibility. A few points to think of. Pulling this way you must have your seatbelt on. You should also have your clutch foot rested on something just above it so if a flip starts you can instantly push the clutch. Also, add lots of weight to the front of the tractor.
I have an arch exactly like you show and have sucessfully pulled big loads with 20 and a 25 horse compact tractors. I have pulled any load the arms will lift. Only on very heavy loads I add a check chain which links the choker to the drawbar using a short chain I had made up to attach to the drawbar, reach back 2' and grab hook onto the bottom of the choker loop. This is a saftey to prevent flipping from pulling too high on the tractor. Try these methods and you should do fine.
But, don't stop thinking outside the box as a general habit. That is how many new ideas and concepts are born.
Dave Klish, I recently ordered a 2x6 wood fired evaporator from A&A Sheet Metal which I will be converting to oil fired
Now have solar, 2x6 finish pan, 5 bank 7x7 filter press, large water jacketed bottler, and tankless water heater.
Recently bought another Gingerich RO, this one was a 125, but a second membrane was added thus is a 250, like I had.
After running a 2x3, a 2x6, 3x8 tapping from 79 taps up to 1320 all woodfired, now I'm going to a 2x6 oil fired and a 200-425 taps.