I'm not convinced you got a bad deal on the property itself unless you overpaid for it and are bleeding because of the loan you took to pay it or because the taxes are super high.  

By the time you factor in vacancy (~5%) in my hood and maintenance (~15%) you're bleeding pretty good ....

Doesnt surprise me in bleeding heart tenant safe haven NY.  

First, I'll say that I'm a bleeding heart dog person.Second, why not just ban the boyfriend's dog?

Please don't take me as a bleeding heart.

My forehead is still bleeding from hitting it against the wall.3 months into a new lease, tenant starts a kitchen fire (unattended frying pan), and I kindly move her into a vacant unit while I fix hers.

Ed Hardy bros like Grant Cardone are bleeding heavily and let go of their entire staff without notice cuz they assume infinite appreciation and a BAM that will carry them through the finish line.

when I am no longer bleeding money from all these repairs?

In my opinion.You are going to make my head swell...I always look at the value add but let’s ignore the value associated with the ADU. 

If I was your wife, I'd be hearing you accentuate the positive all day long and warning bells would be exploding in my head.Just for starters, let's get clear about third-party Section 8 multifamily property management -- the guys who do it are in it to bleed you as much as possible.