The high end is the 20 or so co ops on 5th Avenue or Park Ave (one is on East End Avenue) that require liquid assets of $100 million + to gain board approval.  

., but their lots were like parks.

So, just so I’m understanding correctly, unless the ADU has a driveway for parking of its own, then rent rates might go down on the actual house bc, essentially, the property land is being shared by different parties?

Why would you literally wait until the last minute, when a flat tire or difficulty finding a parking space be the difference between keeping and losing your home?

Look into asset classes with stronger cash flow, such as small multifamily properties, short-term rentals, or mobile home parks.

I would definitely add beach, park, boutique/restaurant shots.

Outdoor storage, moving services, additional parking.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

So, in your considerations, I would park right there for a bit and determine how this would look for you.Since you have about 2.5 years to think about it before you would need to spring into action to take advantage of the rollover for tax advantages, maybe you try on a rental and see how it fits. 

We live in Andover but have one single family home in Park City, 2 in Newton.