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Wasn't really meant as a jab, just if you're worried about the transom supporting a motor that it normally would have no trouble with, you're likely to encounter issues when the entire outboard is hanging off the back (underway) as opposed to when you'd have it tilted up and a lot of the weight would be centered above the transom.

Unless you're suspecting real structural issues, even a Sakonnet that old should be more than capable of carrying the weight of a 60. The M-Y Wedge or any similar trailering "helper" would actually alleviate some of the shocks that your transom would be subject to while you tow it. Also, you'd be avoiding the chance that your tilt piston loses pressure and the entire motor comes crashing down, which I have had happen to me. It was the reason I purchased the M-Y Wedge, actually.