Drug addicts will almost certainly fail in one or more of those issues. 

I have seen it tried too many times and fail.

You're getting ready to turn over one of your most valuable assets over to the person you're trying to nickle and dime and which will ultimately help you define it either as an asset or a liability.... go ahead... bargain all you want but likely you'll be posting on BP with all the other disgruntled owners on how the PM failed you... regardless of what you read or hear it's a universal truth 'you'll rarely get quality service at rock bottom pricing', heck I've got a 19 yo. cousin that will manage your rental for 2%... want to take him up on that?... 

It has been listed for over 3 months with two failed contracts so far.  

How do you justify starting when so many fail?

It is an awesome book with great advice on how to better manage your day to day activities and free up the “mental weight” of all that you need to get done.

I just finished listening to the audiobook version of Nate Silver's book "The Signal and the Noise: Why So Many Predictions Fail - but Some Don't".

If it is something they could not have known, it carries more weight than a "wish list".

Does this strategy fail if there is hardly any equity in the property?

It is a solid play especially, if you think you have systems that will fail in the near term.