If I were a gambling man Mike, and I were looking at CT, not just Hartford, from 3,000 miles away (with limited direct knowledge and experience), I would bet that when CT finally turns over to a more business friendly climate (ie, oust the liberal - long held democratic views), we could be just like you in CA :-) In fact, if I recall CA was in some major trouble 10-15 years ago too, and now look: 2016 San Fran became the very first area to have average home prices over $1 mil. 

Promises were made and then broken.They pushed me hard to go to a free one-day event called "Ignite", so I did. 

I wouldn't recommend going into someplace that has no policy concerning STR, as it's a huge gamble.

The only thing he hammered home was that I should take the 1-day "Ignite" class - which turned out to be nothing more than a huge pitch for the 8-week BOLD class. 

The cash you can "Throw at this" will probably figure into it, unless it's some type of high risk strategy where you have to do X a lot times in hopes of getting result Y (in which case it's more of a gamble than an investment).And as Kenny Rogers said in "The Gambler", "You never count your money when your sitting at the table".Kenny Rogers "The Gambler"But if you are gambling, then realize that sometimes gambles pay off and sometimes they "Crap Out".Good Luck!

While the potential increase is a gamble from zero to infinite, the security of not creating a lease no longer appealing to the company is guaranteed.

It's really a gamble which way pay model is best, per-plow vs contract. 

CON- It's a gamble & if your timeline for returns is short then it may not be worth the risk.

Has the neighborhood improved or is it a huge gamble still?   

Unless you just have loads of money to gamble with.