If something breaks and they're not shopping around for deals with contractors, is this the person you want to be working with? 

I'm working on helping some clients/friends of mine get their condo rented as a medium term rental, but not getting many hits on it, only one person that never answered me back after multiple calls and texts (stay has to be 30 days or longer).  

I know Keith personally I would be surprised if he had a collection situation that was not perfected.

Thanks for sharing your approach!

MANY MANY landlords will NOT rent back to anyone they personally know.

I am hoping to see how I can purchase another property without dipping into my personal funds.

The cost of hiring the right person is significant and may make the whole deal not worth worrying about.

It's a highly nuanced industry that isn't very regulated so you will need to know what you can and cannot do legally and then create some personalized guidelines around what you want to fund and what you want your returns to look like.

Many investors, like myself, just hold TItle personally with homeowners/landlord insurance, umbrella policy, and keep the property in good repair. 

In a “nutshell”What can work - partnerships where each person brings a different necessary asset (knowledge, experience, time, capital, credit) to the table, the responsibilities, rewards, and expectations are clearly spelled out, legal documents are created to head off disagreements, and the parties are compatible.What doesn’t work - partnerships formed by two or more inexperienced people looking for “comfort” rather than going it alone, and anything other than the above.