I would supplement @Russ Seiler's endorsement with a word of caution and a recommendation that you review any "creative tactics" gleaned with a tax accountant and/or attorney before putting them into play.There are still a number of "Rent to Own" providers in Canada who are operating in a manner that is "grey" and out of step with CRA publishings.  

I am pretty certain that Chicago is fine with it as well, even though they are aligned with pretty much any other escrow that will endorse them.  

And with the new president endorsing a bigger navy or military, that could offset losses.

Dustin- you won't get an endorsement from me of any guru, and I WAS one.

No wonder most American companies overseas prefer to hire non-Americans, they don't have to pay them as much.Bryan, you have my email.It is interesting the number of people here who have endorsed the cash purchase of low dollar, cash flowing properties.

Depending on the type of property and the policy used to insure it, there may be endorsements you should consider.  

@Wei Xie @MARK MULATTIERI  You are not responsible for how the check is endorsed.  

I also plan to request they add me as the Certificate Holder and Additional Insured on the policy, and provide me with the policy endorsement.

But there is a ready made homeowners endorsement for this.

If you "misrepresent" (i.e. lie), it's as if you have no coverage as they can deny all claims.Not every insurance company will do this , but some companies will allow you to buy a rental policy and then add a "vacancy endorsement" for periods of time that it is vacant.