Maybe, maybe notYou have to weight the pros / cons along with the risks.Your BP mentions you are 'new to real estate'.You are getting into a new asset class along with a business(I consider a STR more of a business than an investment).How much will you save in taxes?

Is the house nicely kept and relatively orderly?

Nice to meet everyone!

I am a high-wealth earner with years of employment ahead for me, so I will not feel the weight of this loss other than shame on me for not appreciating this risk better before committing.

My owners who have updated their homes with modern furniture packages and highly themed rooms, along with a nicely equipped game room do much better than those who do nothing to the home and hope it will attract some guests. 

Since she is already willing to go to court I know she wont actually leave or pay rent but I want to make sure She cant say on court that she didnt pay because she didnt know how much to pay.2- On November 5th (because thats the date of the notice to vacate I put in because I thought I had to give her 30 days and I wanted to be nice) I will file for eviction.The issue is that I know the previous landlord used to pay the eletric for the house, though the lease clearly states is the tenants responsability.

I'm going to need a great coat of primer, and then I'll paint the walls with Alabaster. 

Very modern and nice.  

The owner built a 1 bed apartment in the basement nearly 30 years ago and did pretty a nice job. 

I'd recommend somewhere other than California.As others here have said, buy your nice house, pay down the mortgage, relax. vaya con dios amigo.