You are gambling when you buy a property that is costing you money every month to own it and your banking on appreciation. 

Essentially what you do is borrow fund at favorable rates, and the security for the lender is provided by a mortgage or lien over the available equity in the real estate asset, and the loan proceeds are directly transferred into an Offshore trust.

Matt  my surfer dude buddy.. this is simply post GFC were the mantra is cash flow is king and appreciation is luck .. and well many many people believe that.. or cash flow is the only thing and appreciation is gambling... but if I look at the biggest hits of my career its been on Non cash flow assets IE NO cash flow or negative but multi million dollar paydays. 

They collect these submissions and if something pops up in your area, and your home potential fits their needs, they will typically do a screening, need more information and if you get selected you will begin talking through pricing, contracts, etc.So if you are switching just for the sake of insurance companies, then it would be a bit of gamble becuase these take a lot more time to foster relationships and build trust.

It's a gamble!

I'm willing to take the gamble on them leaving as I will be able to rent them for $400+ more per month with new tenants. 

That is a bit of a gamble.

But stocks are gambling for most (unless you have insider information or disciplined monthly investing on the index over a long time).

Failing health, gambling debt, legal troubles, divorce, etc.  

If it were closer and I was more desperate for a place to deploy capital I'd be more willing to take that gamble but it's pretty far from Denver, and too different from the rest of the Front Range market that I understand better and have more faith in.