Owner and tenant are friends which is why I guess an eviction never occurred.

If you want a good realtor in this area that knows the market and may even have access to Pocket listings then you need to be talking with @Avery Carl.There are many ways to transact real estate in this area, and you would be surprised how many transactions occur before houses even hit the MLS.

Modern websites and applications require data transfer to occur in the millisecond range.

There were times were the bank I worked at would turn away the business because we didn't want to risk (with our regulator) performing a transactions we strongly felt was prohibited and us ending up getting in trouble as well.The penalty if you get caught is that your entire IRA account (one account where the transaction occurred) is considered to be distributed and therefore a taxable event. 

Now they send the bill to us.The lady at the Office of Tax Commissioner said that we are supposed to pay that bill {$12,770 by December 20th 2019}, even though that issue occurred well before we purchased that property.

(Option B) Now that I am typing this question, it occured to me that we could spend $500 on an appraisal to try to remove the PMI which is around 55$ each month and our cash flow will increase to about $143 per month.Which option should we pick?

MOST ANY COMPETENT REAL ESTATE ATTORNEY WOULD LIKELY & STRONGLY ENCOURAGE YOU TO NOT PURCHASE A PROPERTY "SUB TO" BECAUSE OF THE GOTCHAS THAT CAN OCCUR, NOT THE LEAST OF WHICH IS VIOLATING THE TERMS OF THE SELLER'S MORTGAGE OR DEED OF TRUST. 

The PM isn't making much money on the 8-10% PM fee and they are banking on repairs, turnovers, evictions, etc..The PM will tell you it was an emergency because water was leaking behind the walls and they stopped further damage from occurring. 

I'm working on a direct mail list using unpaid property taxes and It occurs to me that in the area in which I am searching they don't assess a late fee until the calendar year ends.

I am a new home owner in an up and coming neighborhood near Denver, CO where there is a lot of gentrification occurring.