I am encouraged by the expansion of the Blue Mountain Ski Resort, now a 4-season destination.

Hey @Chris Napierala, if you have tech experience, which I assume means web creation and/or programming, then you can look at Wordpress as a hosted platform on Blue Host or some other top Wordpress hosting company.There are a ton of widgets and API's for Wordpress just for STR or hoteliers etc.

I would encourage you to go to https://joefairless.com/work-joe-3/ and schedule a call with Joe.

I would think they in theory would encourage this but know that the wealthy generally own the RE in SF and would likely lobby against the "forcing" of landlords to comply to policies increasing density in their properties.2) For what @Bruce Woodruff mentions above.

Are there other factors that I should consider that would encourage me to pursue this specific market? 

Is it professional to go on different platforms like FB, Instagram and give shout to ask cash buyers what criteria are they looking for?

Here is where I encourage over-analysis (on past experiences filled with valuable lessons).Quick recap on some things to learn, not to belabor the point but the painful review is absolutely necessary in this case:- Always run your own numbers, and even still.. always be skeptical of them.

List on MLS and all platforms.

I've also heard Apartments.com works well too, but don't have experience with that platform yet.

But, I find it a little shady that they boast "their" SEO features as a reason to pay for their platform when they simply rebranded a free plugin and slapped "Carrot SEO" at the top.