Thanks Ari and James for your input..Looks like all cash is little profit, but no stress, and you own the property free and clear, as well as can sell it for 100% profit..

Okay, the timing sucks, but for $5k (you're not "losing" the $10k from the higher offer, since you don't have it to lose) you're creating way more stress than it's worth, @Alex Kovalenko. 

Also can’t stress this out but if your going toward (working with an agent) be sure they are investor oriented in properties you seek to purchase .

My questions are: how do I approach the conversation that the goal is to help them get out of a stressful situation as well as making a good business decision for myself?   

That's what many tenants would feel and do ..... but in the back of my mind that stress of doing that would still linger with me... not something I have EVER done beforeBasically I'm pissed that my wife for even put us in this situation by signing the lease to begin with...

Slacks and a button down?

It seems easy and exciting-- Roofstock.com has a "buy it now" button, for Pete's sake (don't do it!).   

I do not want to put them through the stress of another additional expense.

If you don't want turnover, it often makes sense to have smaller (or no) rent increases on reliable low-stress long-term tenants.

This too shall pass.Interestingly, this is exactly the reason that loan underwriters "stress test" the financials on properties and require things like a 1.3 Debt Service Coverage Ration and cash reserves.