Cool cool. Well in that case, the metal rod that goes through the bailed hole may not be far enough in to the bung. Mine comes right through the rubber and protudes a good few millimeters before it is watertight. Try pushing it further on to the rod while the bailer is open.
I have read a few things the past few days that would all have been made easier with a small dolly to rest the bow on. You could then just lift at the stern and push like a wheelbarrow.
if you aren't racing it could easily be bungeed to the bow eye on the deck too for when you get back in...
I recently bought a 79000 era boat. That is about 25 years old so yours would be slightly newer. I payed £375. It is a fantastic condition Hull, stiff, mast step in good state (holds water )
It didn't have any xd style rigging on it which I wouldn't expect for the price I paid.
I think a swivel cleat used to be a builder supplied option so I wouldn't just assume it's not legal. My laser certainly looks like it came with one although it was removed thankfully.
Why not precapsize it?
At our club, in a blow, we will pull the boats over and rest them on the bank. Stops bucking booms making dents in masts/wind indicators when there are a lot of boats on the jetty.
Re: Trailing on gunwale hing trolly/trailer
I think they are to overcome the problem of trailers usually not really having very good suspension. Large jolts transferred directly in to the gunwales on the road are more likely to damage the hull than a short period resting on the hull.