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I believe most timeshare owners are contractually bound only to sell to individuals, not to LLCs or some other legal entity for this exact purpose.

Couldn't you just find a real person who is on the verge of bankruptcy and offer them $10 to take the timeshare?

Sounds like fraudulent conveyance.

Reading https://en.m.wikipedia.org/wiki/Fraudulent_conveyance it doesnt seem like it fits to me, but ianal.

Oh because a contract that is like a cronic disease is the highest point of lawfulness

It's not a question of what's lawful or not, it's a question of how much of a pain the litigation is going to be.