We have a guy we use for general maintenance that does good work for us and pay him with Chase QuickPay.

If entered, that would give the police an excuse to arrest the three and keep them in jail longer.Fourth, when they're arrested/chased away, can you take their belongings and throw it in the trash?

This Deal was actually a Short Sale through Chase In 2014 !

After a lot of calling around to big banks, I quickly found out if it's not livable, the big banks (Chase, BofA) won't touch it.  

Chase, I agree with the mindset that you have to consider outside of Chicago for landlord as well as tax reasons.

.---- Skelton: California’s housing is a mess — and Prop. 10 won’t helpThrusting all the burden narrowly on developers and landlords will chase them off when they’re needed more than ever.https://www.mercurynews.com/2018/10/09/skelton-cal...

Seems like paying off one property, as you suggest in option #1, to eventually refinance it to buy another property is just chasing your tail. 

In practicality banks aren't usually chasing due on sale foreclosures, but if interest rates rise there might be a business decision to go after these to increase their interest rate yields.

Many answer this buy reducing their criteria for what a "good deal" is (why in the ...) because they are chasing the property instead of the deal. 

The lawyer is going to chase the money not you.