Your pic of the winch/ rubber stop.....
I would not have set that untill established where the boat travels best on the trailer....1/2" can make a huge difference as we discovered.....Fortunately our V rubber stop was mounted a little to far towards the tow ball...(this position the boat towed ok but had a tendancey to occasionally get the wobbles.....2" further back, was sort of to light feel on the draw bar....
I established the best position by pre making several spacer blocks out of wood... and changing on the side of the road on one of our 35 min trips to the ramp
Also.. something Im currently looking at .....
I have been watching my new winch ...
Couple things are not 'right'
1/
The boat 'load' when trailering is on the winch... well the winch
bearings, which is not good for them or the winch and how the gears
align long term.
2/ To find a chain/ shackle combo that fits so exact
one can back off the weight on the winch very little change in boat
pressure on the front V is near impossible .. and impossible in our
case.
So i have been looking around for an 'adjustable '
suitably rated shackle system.... a turn buckle....the problem is to
find a turn buckle of the correct rating but sort enough.
I
have looked around the ramps, and it seems there are a lot of winch
bearings that have been 'pulled' in their seals, and its general
practice to have the winch as the primary holding force for the boat,
and the stronger chain shackle as the safety.....which to me seems very wrong
And maybe something else to consider.. and covered in some older threads.... I pull our fully laden Commander (less ppl) up on the trailer with a old 2nd hand 18v black and decker battery drill with a deep impact socket with slots in home made adapter... and I do it faster than can wind it on myself