I'm also entertaining the idea of staying put and just taking out a big HELOC, but my fear of getting stuck in this house and town is significant.....I don't gamble at all, and I don't watch sports.

I would prefer to immerse myself in other markets that do cashflow and where there's more houses up for grabs, Instead of swimming upstream.  

I appreciate your comments about providing ongoing education but it seems even this is a real gamble.... at least for the renter. 

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?

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 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.

Investors Wanted To Believe though.....I saw people pay $50k Over the HOA judgments on that gamble......a nice surprise for the homeowner who hadn’t paid his mtg for 6 years......not so good for the buyers.