Any type of 12-volt winch should work just fine - 60 feet isn’t that far, and you’re well within the weight limit of the cheapest winch. (Even a half ton winch could safely lift 330 pounds.)

For your trolley, I’d look at making “rails” from L-channel steel. Put the vertical piece in the outside. The cart can just be a square of steel with some roller skate wheels on it. They tend to have good bearings and are fairly durable.

The advantage I see using the L-channel is that you can go over whatever your existing landscaping is - you could have flowers, grass, etc. in the middle, and the cart should mostly just push them out of the way.