Project is done-here are my observations/tips using a 39 HP tractor, Tractor supply subsoiler, and 1" black polypipe:
1. Can't really control the depth of the subsoiler - it will track up and down as you go along so if you have to get the pipe to a certain depth, it's not super reliable
2. Soil has to be just right - not too wet/not too dry. Made 5+ passes when the soil was too dry and didn't get the depth I needed.
3. Tried making the sleeve out of 2" pvc. Filled it w/ sand and warmed it over my grill till it was flexible. But in the end, the friction through the tube made me give up. Would've worked better w/ larger diameter tube.
4. Ended up using 14 ga wire and wired it to the subsoiler a couple days after it rained. Pulled it in 300 ft sections and it went in smoothly. Wanted it 10+ inches deep even thought frostline is around 8" (southern OK). Not sure it's all going to be deeper than 8"
bottom line opinion: should have sprung the $140 to rent a trencher and know my depth. Would have saved me on time and failed attempts.