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I can't help but notice that this discussion has devolved into a pie fight that is only tangentially related to the original question, and the OP isn't participating.
StillSearching, if you're still there: I wonder if you actually need the bolt on extension you're talking about. You say your bed length is 16', my Toyota pickup is 15' long. Just how big a car are you wanting to be prepared for? And standard lumber lengths from the big box home centers top out at 16', so that's covered too.
As to tipping the trailer on its side, that gives me the willies just thinking about it. I'm not saying it couldn't be done, I'm just saying I would hate to have to do it. You'd have to be 100% about getting things lined up for a perfect tip, because it would be crazy difficult to scoot it into a better position if it wasn't right once it was up.
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Lead or follow. Either is fine.
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