Admittedly, I am unfamiliar in this space but it appeals to me for a few reasons.

A home that sits on the market quickly loses appeal.

You’ll cut down on the chances of a long leasing process by appealing to what is most popular

There is a lower probability of adding value or appreciation over time with this IMO, but it has appeal that should keep it stable as an investment and be an enjoyable one to own (and possibly to maximize any time of vacancy in the unit with a site-visit + skiing?)

If I can’t deliver anything appealing enough he is obviously going to play it safe with his broker in SF and just do a similar project to the previous two. 

On other occasions, it is also possible that the prior owner appealed the former tax assessment to get a lower value.

And being on-call 24x7 isn't terribly appealing either!

I have always been interested and felt drawn to Real Estate as the appeal of owning a tangible piece of land has always been attractive to me.

The thought of getting money out of my primary residence now without the monthly paymets of a HELOC or refinace is appealing but not sure if it worth it in the long run. 

The Subject 2 deals strategy or technique seems very appealing to me.