You have to be a specific type of person and be comfortable with strangers sleeping in your home, but I think once you get over how weird it is at first it can be a cool experience. 

Cool. 

So I’m wondering if I should jump in to the real estate game now and start working forwards my goal, or should I keep hoarding money away until the market cools off a little bit.

Asset protection is key concept that I picked up from Rich Dad Poor Dad book "Unfair Advantage" by Rober Kiyosaki, and my limited understanding tells me that I should have an LLC to protect my personal assets from the property, that is a cool $800/ year here in California.

I love em because they work at any point in the market cycle (about to get even better with the market cooling off) and you don't need lending or any capital to do sandwich lease options and if you do get a home at wholesale pricing (70% of value) you can then purchase it with private lending for usually 1% above prime rate to still mortgage it medium term (<5 years) and make a larger profit when it closes.

I'll bet that feels cool to go and visit a property after you've bought it. 

Not cool to lock up a property hoping you find a buyer, wasting the owners time (and money if they have financing on it), and getting their hopes up, just to walk away 30 days later.

Not as cool as I thought it would be. 

Edit: Shoot, can't believe I didn't think to add this as it fits my interests, but I think the Smart Home/Automation trend is really cool and hope to be able to get more involved with that.

But with this type of saturation in high-end units, which I hear is happening in other metropolitan cities, a cool-down is all but inevitable.