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RE: Would you let a stranger sleep in your home for $100/month?
No. Your home needs to be a place you are secure and can let your guard down. You want to strew your prized possessions about with abandon. I've had boarders before - I like people for short periods but very quickly I find myself wanting my own space again - ymmv. Family and friends I just let them stay. If they stay for a while they'll often contribute in whatever way then can but I don't have expectations. But, with long-term staying with a board/rent changing hands it can get messy fast.