I know that appreciation is a gamble, but if a city's economy is diversified and there is a finite amount of land in the prime location that is downtown/waterfront then chances are it should appreciate, right?

Best of luck to you and your family on this new and exciting adventure!

I would start your adventure by checking out the local Meetups in the area.

But of course that’s the gamble. 

If I want to gamble I go to the casino.

I'm utilizing both of those stock options and feel it is in line with my "gamble" on the company as a whole, if all goes well and they grow and show a profit, it will have been a great investment. 

I will be self managing, and like most of my adventures, I tend to wade into things rather than jump, sometimes to my detriment.

Best of luck on the adventure!

I think I have got enough knowledge and capital to buy my first SFH or duplex rental property, but my wife thinks buying rental properties is gambling.

That is exactly what I see, buying condos from a wholeseller seems like a real gamble.