Drive em up or winch em up?

[VETTEGUY]

Here's my rule of thumb for putting a car in an enclosed trailer: If I'm alone, I always use a winch. For me, it's very difficult to judge position from either side of the trailer when pulling in. I usually run into a wheel well or at least scrape a tire against it. You did the right thing to increase your towing capacity. A half ton PU will not safely tow a 22' trailer at highway speeds. Many will say that it's no problem for them, but they haven't had to make an emergency stop-YET. Best of luck to you.