Taxes of $4,300 annually and homeowners insurance are paid separate.

I apologize for the miscommunication, I meant that the rehab cost estimates I received from 2 separate contractors deviated from my own between 2-5k.  

For each of my properties I have a separate bank account, checks, and a debit card.

In some areas, you'll need emergency egress, heating/cooling and separate metering as well to be considered a triplex.

Sorry to heat about tenant situation.Understanding that you should not let your emotion get into your decision making process is also a big plus.Good Luck on your next one!!!

I financed the property using (i) a conventional loan and (ii) a HELOC on the property that was drawn at close (there are two separate mortgages on the same property). 

On bottom of garage separate from Airbnb is an office/entertainment space with restroom, fridge, and oven about 400 sq ft. 

The upstairs has a separate entrance and is currently rented $125 below market rent.

There's definitely a human (emotional) element to this scenario, but from those more experienced...are most sellers in this position open to further questions for understanding the property or do they tend to be a "you get one shot, make it quick" kind of thing?

I know its probably an emotional house for you ( mine is also) but try and run the numbers on what your monthly cash flow would be if you sold the property and used that money to buy 1-3 investment properties. idk your market but in mine that extra 150k could easily buy 4 (maybe 5) properties that would cash flow a minimum of 250 but most likely 350-400/month.