I've flown (speed) off pylons that were set into the ground, and pylons that had a steel base plate about 3' dia., made of about 3/8" steel plate. I preferred the ones that were set into the ground, because I could let the pylon take more of the load. Since you seem to live on some acreage, I'd suggest putting a socket in the ground. Tim may have looked at the details of the pylon socket in Salem. I suspect pipe nipple/coupler buried in concrete, flush with the ground?
Most only had a 3/4" steel pin sticking up out of the pipe for the pilot to hook his thumb around. That works well, but of course, isn't good practise for flying on a pylon that is made per AMA regs. It's not going to make a difference in the speed timing, but it's not per regs. But for your use, the simple pin would be my suggestion.
If you do this, put a pipe plug in the hole when you take the pylon away to the barn, and use some anti-seize on the threads, etc. I think 2" Sch. 40 pipe would be ok for your purpose, maybe 3" for a real speed pylon. A pipe cap at the top with a pin welded through a hole in the center would work for the top, or another coupling with a plug and the pin welded through a hole in the center. You'll need to figure out how long the pipe should be, and I suspect it would be good to recess the socket a couple inches so the pipe plug doesn't get hammered by the mower blades. Probably set it in concrete?
One more thought...55' lines will be way short for your big'un. I might start with 60', but if you've done your bench trimming, 70' will be safe if you've got the room. Measure twice, cut once!

Steve