I don’t believe so. The game gives you plenty of free trailers and you always have the option of purchasing more. Won’t be too long before you have the means of retrieving that stuck trailer.
For trucks, as long as you can switch over to the truck and essentially claim it, you can recover those from anywhere. It took me awhile to figure out how to switch to trucks out in the field via the map, but it’s doable, so you should never end up with a truck that’s truly stuck.