The downside is you lose the experience of someone else with more or different experience than you, my guys have helped me avoid a lot of major issues through the years that I would have missed. 

I'm sure the interest rate is high and at some point you will begin to lose money. 

It is the "guts" of the evaluation that will tell you if you win or lose on it. 

The answer:  Stay in the game.If you continue to hold a property that is taking your cash (negative cash flow), you will be out of the game just as fast as if you were to keep putting chips in the pot of a really bad hand.You haven't lost any money when you lose hands in poker, just like you haven't lost any money when you have negative cash flow...as long as you still have money left, and you get out of those bad "deals". 

I was literally depressed for about two weeks about losing this one.

Like flying over to Catalina is super cool and mixing it up with atc flying through the LA basin .. brings back your radio skills  that we sometimes lose when I am mainly flying rural NW.. and not talking to anyone..  

But I lose 1 month rent for that service.  

@Jorge Barboza Jr.Tom is right, determine each player's roles and contributions, including time, talents, and money.You may even decide to have one party active and the other passive. 

With debt free you lose a little arbitrage on interest but gain a lot of security and control. 

In many areas, you will lose your shirt paying 100k for a house, and others you might be ok.ARV is hard to know in Savannah since taking comps even from a few streets over can be a folly.