If its negative cash flowing NOW and you don't have a ton of reserves to cover yourself long term for the HOPE/GAMBLE of the appreciation play, then its time to sell, cut your losses and move on

Some times it can work and the gamble pays off, unfortunately it usually does not.The numbers starting out look good enough to try you only lacked the experience to succeed.My advice would be to stay away from real estate.

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 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.