You will spend around $10k fighting with this borrower so at the end of the day you would may $15k over 1.5 years and be all in at $100k which is aruond a 12% IRR. 

I know of someone locally in San Diego that moved all their properties into a trust using a specific attorney and all of his property taxes were reassessed, double or tripled and he's been fighting it for over a year.

Been fighting with insurance. 

They know the system and they don’t want to go down without a fight.

The court "likes" this better than the judgement, takes away the fight with the attorney and gets you the possession back.Sometimes the tenants don't show and you win right away - yes, that still happens.In the end, @Nathan Fisher is right on, you need a good attorney. 

The PA came through big in the end, and was the subject matter expert that I needed to represent me during this process while fighting the insurance company for proper coverage. 

Being one not to back down from a fight, I fought and argued that it was an ADU.

@Steven D'Agata fight taxes.

Ordered a bunch of those metalplex metal decorations for the whole cabin and only 1/4 of the items arrived, been fighting them for months for a refund, horribly run company.Spent a lot of time yesterday and today filling out more fields in the listing, adding captions to all photos, adding additional details, hopefully that helps us rank higher we will see.

This way you could focus on your job that brings in good income and not have to worry about finding the deal, getting it under contract (while fighting everyone under the sun to get the property) and managing property managers/tenants/toilets?