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Jim -

Before you spend some serious $ on a winch, check your trailer.

If you have an all bunk trailer, consider adding slide sticks or convert to a keel roller/bunk trailer.

Both of my boats had terrible trailer setups when I bought them. Once I fixed the rollers and adjusted the bunks, the boats would slide off with a gentle push and winch on easily.

I trailered 100% and know those steep ramps you refer to. Eliot, Maine is quite fun.

As for Harbor Freight, you get what you pay for.