So as you can see, Saturday I got my first pole lifted. It took longer than expected, but in the end I learned a ton and am confident that 3 of 4 of the remaining poles will go quickly.
Last weekend I failed to lift the pole because the area around the hole was so marshy that I couldn't get my truck into position where I needed it to be. The ground was a little damp this weekend, but much improved overall so I gave it a shot. The pole was in perfect position where I left it last week. I got the truck into position without any difficulty, got the chain around the pole about halfway up its length, attached the chain to the comealong, and attached the comealong to the tow hitch of the truck.
Attempt #1: Using the comealong, I pulled the pole into the 2x4 backstop. From what I read on the Internet, at this point the pole is supposed to begin lifting because the backstop is preventing the hole-end of the pole from moving... In reality, I just kept pulling the pole tighter and tighter into the backstop with no lifting going on. I heard the backstop crack, and decided that it wasn't working - I was getting lots of pull but no lift.
Attempt #2: I moved the pole out of position, and dug a shallow trench (maybe 6"-8" deep) to try to angle the pole downwards into the hole enough to get a little lift. I put the pole back into position, pulled it into the backstop, and discovered that I had not fixed the problem... I was pulling the pole into the backstop, but now I was hitting the 2x4's under the ground level. So the 2x4s were no longer in danger of breaking, but I was still getting no liftoff because the flat butt-end of the pole was still pulled tight into the 2x4s. I began to doubt myself a little.
Attempt #3: So when in doubt, add a chain saw to the mix. At the butt-end of the pole, I sawed off a small triangular-shaped wedge to create a pointy linear "hinge" upon which the pole could rotate upwards. I also had plenty of chain length left, so I moved my attachment point further up the pole to lengthen my torque arm. I tightened the comealong again, and still no liftoff, but it seemed like the pole might have moved a little. Suddenly encouraged, I knew what I needed to do.
Attempt #4: I moved the pole back out of position, dug the trench maybe another 2'-3' longer and down to 2' deep at the hole end in an effort to increase the pole's angle even more. I put the pole back into position, pulled it tight with the comealong, and started cranking. I had my back to the pole to do the cranking and suddenly something changed - maybe something started sounding different. I looked over my shoulder and was thrilled to see the pole a foot or so off the ground.
One thing I learned immediately is that the trench was keeping the pole from swinging side to side, so no guy wires were needed. I cranked the heck out of that comealong until the pole was at about a 70 degree angle, then ran into an unexpected issue. As the angle of the pole increased, the angle of the cable also increased. Since my comealong was connected directly to my tow hitch, as the pole got higher I found my "cranking angle" between the cable and my tailgate significantly decreased, so that near the end I could only catch a single tooth, then eventually no ratchet action at all. At that point, I jumped in the truck and very slowly pulled the pole the rest of the way. I could tell the pole was in position because when it fell into the hole, I could see the chain go slack in my rearview mirror.
Since Saturday's R&D took more time than I had expected, I spent the rest of the day moving the 2 newest poles from one end of my property up to where I'm building the wall. The big pole, which my wife has named "Monster," is going to be a challenge. It is so big & heavy I'm going to have to engineer the crap out of the thing. That said, I now have my proof-of-concept and have lifted what I consider to be my 2nd biggest/heaviest pole (after "Monster"). Weather permitting, it is the next pole I'll try to lift next weekend.