Playing the appreciation game can be like gambling, and if your house is really cash flowing well after all of your expenses and your mortgage payment I'm not sure if it makes sense to sell. 

Say, you're a sports car fanatic and you go to a sport cars event.

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.

For example, the Franklin Urban Sports & Entertainment (FUSE) project will likely raise surrounding property appeal (and values) significantly.

I would recommend dressing up in either a suit or nice looking new sports clothes. 

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?

So Cal has a broad based economy, perfect year round weather, amusement parks, sporting events, universities, world class medical care, etc.