I have a maybe two friends I’ll haul for (my gooder friend I do this for more often just got her own!) and I do not let them pay for anything. It’s called a favor. Thus far nothing egregious has happened. I am, oddly considering my mine-mine-mine-possessiveness, more likely than MOST trailer-owners to loan my trailer out, however I will say that most of them are farmy or have a CDL (firefighter friend (CDL) with a horsey daughter (and once his motorcycle broke down and he needed to go get it, having a trailer with a ramp is amazeballs) used it the most, but now she is with a trainer and trailers with them). I do have my trailer insured as a separate entity, and include a chunk of money for contents, mostly thinking about theft of $$$ tack but horses are also contents. But there was a good period of time that I had a trailer and never went anywhere, so getting it moved around was a benefit to everyone.
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That’s probably a good plan. I should look into similar
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