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. 

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

And you have chosen a software program that is popular with CPA's.If you are an employer and an applicant applies for a position with you and hands you their resume done via an Excel spreadsheet, versus someone who hands you a professional resume done through Microsoft Word or some Resume software program, which one would you think would be the best suited for the job, based on both applicants having the same qualifications?

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.

They allow tenants to fall behind and prey to their chosen deity that it will work out, which it never does.

You have chosen poorly!

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.

Look at properties with your chosen realtor(s). 

We have roughly $2 Million in equity today and generate enough cash flow each year to support our chosen lifestyle (which is admittedly pretty low key). 

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