OK, gotcha. I thought you were talking business owners.
I paid off my dump truck with basically one big job. Hauled logs off a property periodically for 1.5 years. Also did many other smaller jobs.
I just don’t want to pay the upkeep and $1,500 annual registration anymore.
Tags and upkeep on a large dump trailer? 8 tires at ~ 300 each, batteries at $200+ each, brakes?
Your commercial work pays for what you have, ok no problem. The OP doesn't sound like he is in that situation. May sound like I am against either one. that's not it.
As a homeowner, it really becomes a luxury item and upkeep is something that trucks/trailers need.
A $10-15k trailer sitting in the yard being used once or twice a year costs between $83 and $125 per month for 10 years, without any upkeep (tags, title, insurance, etc.) Is it Convenient, yes necessary, maybe.
We have a dump trailer at the farm and some days I'd give it away. flat tire, bad battery, lights dont work, brakes, latches, tarp AAgh. Always seems not me and I don't know were the last people to use it.
Its not up to me to make choices/decisions for anyone else. My opinions are expressed as to why or why not I would do it.