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Yes, easier to work for strangers.

A sawbuck makes easy work out of that smaller stuff, many pieces at a time, upright, and away from dirt. You can find a good pallet-sawbuck video for an idea. Easy for the HO to tell the guy cutting the wood up.

Depends a lot on your financial well-being, their financial well-being, the costs and risks involved, and relationship. I suppose, also, if they are broke because of poor financial management, its possibly an enabling action. Easy to give away a quick pruning job or knock over an easy tree...