Assume $1500 - $2000 mo for rental income and assume PITI at $1800 with 6% interest, you are already at break-even.

If they've been horrible tenants, I would never consider amending the lease-break the lease, have them pay whatever the penalty is and get new tenants. 

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Basically for us, a 10-25% downpayment won't make any of these properties cash flow, let alone cover their expenses to break even.

Most likely won't be breaking even. 

All of these areas are STR-friendly, which will increase your monthly income significantly, and at least bring you to a break-even point. 

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Just because you add an ADU doesn’t mean it’s going to add enough value to recapture that $300K.If it sounds slightly out of your comfort zone a simple conversation can be extremely impactful Thats where breaking down the payment management tools, local experts on small repairs, credit and background checks for renters, all comes into play.

I want to make sure that I'm not breaking any law that would result us in a bad situation down the road. 

But in our area some real estate agents do represent both sides anyway and may even give a break on their commissions when doing so.