This house has given us great momentum that we want to keep going and some emotional attachment - so we're uncertain on the best approach with this property that is currently making 9% C/C and has continued to appreciate.

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!!!

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.

Just as important to the financial/legal structure is the emotional structure you put in place and few think of this part upfront.  

AirBnB has grown radically over the past few years and these emotional bidding wars for cabins by people with zero REI experience are appreciating the prices vastly higher than the admittedly high inflation rate. 

Anytime you are emotionally attached in investing, it will come back to bite you.

Sometimes my emotions get the best of me.

You are emotionally invested in your first deal and maybe feel bad for the sellers, but it's not your fight.

"Just remember, never get emotionally attached to a property.