As to #1.
My personal opinion, I'd get rid of the strap on your winch and go with a 5/16" steel cable. In my opinion straps are fine for smaller boats but I prefer cables for 20' and larger boats.
Use some kind of boat strap..either belly or stern, to keep your boat from bouncing on the trailer. (Personally I like the belly straps, but I know that lots of guys here like the stern straps).
Use a short (18")? separate cable (or chain) attached to your winch post on one end and to your bow eye on the other end as a safety measure while trailering. That way if your winch or cable or strap should break,
the safety cable (or chain) prevents the boat from sliding backwards off your trailer.
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1987 V20 w/1987 150HP Yamaha on a Shoreland'r Trailer
1978 16.5 Airslot w/1996 120HP Force on a Four Winns trailer
1996 V21 w/1993 200HP Mercury on a Shoreline Trailer
All towed by a 5.7L Hemi Durango.
If God didn't have a purpose for us we wouldn't be here, so
Live simply, Love generously, Care deeply, Speak kindly.
(Leave the rest to God) 
Silence, in the face of evil, is itself evil. Not to speak is to speak, not to act is to act. God will not hold us guiltless.
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