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7 4' sections unguyed. That's good to know. I've got 16 of those sections in the corner of my office in a duffel bag. I rigged a guy-line harness out of some local materials but I've not gone beyond 5 sections.
All I need to do now is sort out the best way to raise it while using the hitch holder like you've got. With 5 sections I just lifted it straight up after it was raised. It wasn't too hard. I doubt I'll ever desire to build a 60' vertical out of all 16 of them, but 8 still might be a challenge. I'll probably end up guying it with a little slack and lifting it straight up after it's raised. I should rig a harness so I can get a better grip and use my legs to lift it in. Or I'll order pizza, bring beer and a friend :)
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Seven sections isn't too bad to lift by hand as long as the antenna isn't heavy. It's a little hard to describe how I do it, but here goes:
Mount the antenna to the top-most mast section and attach the coax.
Lift the first section with the antenna and add another section below it.
Lift the two sections and put the bottom one into the flag holder.
Get another section ready by leaning it against the flag pole holder or holding it between your knees.
Lift both sections out of the flag pole holder and slide the bottom one over the one you're holding.
Lift the three sections and put the mess into the flag holder.
Now the balancing act gets more difficult, but the process is repeated until you're uncomfortable balancing the upper mast sections. Be sure to use both hands to stabilize the upper sections as you assemble them.