Re: Winch
I am just starting to look a little harder at my trailer setup since I am at the age of repair. So you are saying that the proper trailer setup should have the bunks level front to back as measured from the "trailer"? ground? I have never checked mine, I think I will this weekend.
The conflict is that more slant is good for launching and bad for retrieving (which is a function of tilt trailers). Too steep a slant can in some cases cause your transom to hit the ramp on launching if you launch "dry."
If the bunks are level on flat ground they will generally be slanted correctly at the ramp. But there is no harm in having the bunks slanted to the rear some; that slant will be increased at the ramp. So if you regularly use a particularly steep ramp, you could compensate some by flattening the bunks.
What is crucial is that when the boat is stored on the trailer, the slant is enough to drain the entire hull--this is enhanced with the tongue jack. If your jack won't do this, you may need to add some slant in the bunks. This might also be a factor if you regularly park on a down slanted surface, such as backed into a short driveway.
Driving, the trailer should be level and balanced correctly; I don't see how bunk slant would matter any.
All this also applies to roller set-up.