Re: trailer winch size
Possibly.
What is the weight of your boat? What type of trailer? Roller or bunk?
If I recall rule of thumb is that for a shorter pull on a nice easy rolling trailer you could pull between 2400 to 3600 pound boat with a 1200pound winch. If you have bunks and a longer distance to pull with the winch, as little as 1200 pounds.
So your 2000 pound winch could be good for up to a 6000 boat, or as little as a 2000 boat.
Those figures are from a winch distributor I've used in the past.