First post and yes I have searched extensively for the answer. I just bought my first sailbaot Hunter 18.5. I specifically wanted a trailer sailor so that it could spend its nights with me in the drive and not on one of these shady over priced slips here in Texas. That being said this thing scares the hell out me. I have found from the forums that the winch is mounted way to low so I plan on fixing that tomorrow. My main concern is that this boat feels like its going to roll of the trailer at every turn. This may be my green horn coming out, but it makes me sick to think about that nice new paint job laying on the highway! I see these boats up on jack stands with no side support at all. Is the keep weighted so much that these boats just don't tip over? I can see marks on the boat where the previous owner strapped it to the trailer (and the cracks in the glass where they were over tightened). I have read both strap don't strap. I use 4 rod saver 1/2 ton staps on a 16 foot bass boat. Now I have a boat that is much bigger (relative to bass boat) and it has nothing but 2 flat boards to sit on and the winch eye? Am I Just worrying about nothing?