Still, I think you'd find it difficult to find one that would be a good long-term investment unless you had another ~20-30 years to go, it's at least cash neutral, and you don't plan to hold it too long (to avoid too much investment loss and before you get to the point where it's unsellable because of too few years left); that's another way of saying that maybe it suits your cash needs in the near-term or is at least less of a pill to swallow than other options until you find something that's more of a sensible long-term play

People’s Republic of Asheville is more concerned with STR regulations than people living in boxes on the streets.

Everyone has the right to write about their experience but I would be more inclined to pay attention to the review of someone who has been playing video games for years than the person in your example who purchased their first Xbox with no past experience.

You can put an agreement together where you capture any depreciation (if your tax burden is higher than hers) rather than split 50/50.

That might mean only pain $10,000 rather than $25,000 that a contractor might quote you.

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Lots of loan options can close in an LLC, helocs usually need to close in your personal name.

In southern CA, even garage conversion ADU additions are typically costing more than the value added.  

The biggest 'danger' I've experienced in the coaching space was coaches who took the cash and wanted me to follow 'their' program rather than coaching me where I am to get where I wanted to go. 

My experience with the smaller multi-family units has been that more occupants = more wear and tear on your property so the turnover costs are often higher than SFH.