Once you start to find something wrong with almost every deal but finally find one that really makes sense, run it by your mentor to see if they agree it is a good deal.

If it's not an ADU, then you have no limit   Makes sense.

When it comes to a lifestyle property, it's another ball game and all the comments you wrote make total sense, especially for people who like similar things in life.

Confirm that the warranty applies to the type of property you own and consider whether the annual cost and service call fees make sense compared to just handling repairs yourself or using your own trusted contractors.

I sense that your real dilemma is the trapped equity. 

At that point I dont know investing would make any sense, I have heard scary stories I was thinking about short term rentals but that needs constant cleaning after guests and conpetition is very high my friend spent almost 200k out of pockets to buy a property for airbnb and he got 17 bookings per year....

If your properties are bread and butter, cash-flow kings, with low rates, it probably makes no sense to cash out refinance. 

Very cool piece of real estate, unfortunately it doesn't even make sense at the $650k asking price.

If I sense the buyer is cut from this fabric, I will negotiate extra hard against repairs to the extent they simply walk.

Just walk away if you sense they won't let you investigate any aspect of the property you wish to.