Problems in the past are almost always from the Airbnb bookings so I'm definitely not losing any sleep over it, but still scratching my head. 

While I’m happy to share lots of information with folks it’s very rare that I will give out information like my primary contractor’s name or the names of any of his subs because I keep them busy full time and am not willing to lose my own time with them to someone else.

Let her go, get the place treated so it is 100% roach-free, and then find a new renter.At the same time, I would have an attorney draw up a letter hammering the HOA for not stopping the roach problem because it is costing you money to continue treating and you are losing rent income.

I can't sell because id lose my butt on it.

Sounds like you're aiming to make some type of algorithm or software that tries to eliminate the need of competent real estate people utilizing their experience in markets they are very familiar with..........Didn't Zillow lose about $500 Million flipping houses using this exact type of model? 

However, to the other agents points above in this thread, you might be sacrificing not only time, but also likely lose out on a great deal of profit (over what you would pay a listing agent in commission). 

I was concerned that the houses don't meet the 1% rule but with older houses, you're losing in more repair costs. 

Just ask anyone who has been at it for a few years, or follow these forums and read all the threads like this one where an OOS investor in a “cheap” market realizes they’re losing money instead of reaching financial freedom through cash flow.

What do you have to lose by sending them rent increase letters to see how they respond?

Where as if you have an eviction with a single family home, if you have an eviction you lose money, and fast.