More importantly, when you are looking at your exit scenario of selling, the same question applies but in reverse, are you calculating the new tax rate the next buyer will pay and reverse calculating a sale price based on the market cap rate?

I have identified properties in a particular area I want to target and want to reach out to the property owner to see if they would sell.

It seems like the only people that actually know much about these are the people selling them.

Pennsylvania even had cases where lawyers were disbarred for selling overly complicated trust structures to older clients who didn’t need them.2.

If the answer to both added questions would be "yes", then you have a potential goldmine here.Combining the seller's concerns, and the reality of a big down payment being a negative to the seller (see Q: 1), you should be able to set the terms, with a lower DP, and controlled interest rate, to have this property CF and,...be able to sell the package to another REI down the road,...as long as you buy this using an LLC (a new one). 

If you've enjoyed a lot of appreciation in the value of your primary home, you may want to start a timer to sell before losing the "lived in the house for 2 of the last 5 years" capital gains exemption (limited; not infinite, but big).  

They sell you on the platform before you can actually get in and play around.  

I’m thinking it might be tough to sell down the road also however.

Sell the DADU for $500k-750k+ (or keep it as a rental and cash out refinance.)6.

DOM for selling is up to ~80 days.