However, my guiding principals are to lean in to automation, processes and procedures, and ultimately a passive investing time commitment.Emotional Bias: Emotional decision-making can be a significant challenge for self-directed investors.

No standardized processes, no rhyme or reasonm,just  driven by emotion or ego. 

Remove emotion and you'll see he's not at your level.

As you can probably tell, this is not my specialty as I'm answering more generally and emotionally rather than with cold hard numbers.

It's numerically better to pay the mortgage early and it's emotionally and relationally better to pay them back early.

Especially if it’s rental property with no emotional attachment.

Although it is difficult to remove the emotion of managing your property, you need to operate as a business.

And, they have shown solid returns, when I include the Cash flow, appreciation and mortgage payd-own.So if you are patient, long-term, and are able to absorb some bumps in the road (financial and emotional) , you may have a good plan.  

Keep rational and don't get emotional.

I suspect that you and the family are still emotionally attached to the old homestead and you are wondering if you should keep it - do a business Bed and Breakfast - or take the cash and give up your attachment to the old place ----- well ---- only you can answer those questions ---What would you do with the cash - pay bills - invest - savings - vacation - give most of it to the church -?