What is sadder than "it might have been" is "it could have been". Have you ever prevented a good "it could have been"? Regrets?

Seriously? "Might" means it was not guaranteed. It means there was a possibility. "Could" means it would be. "On the Waterfront" says it best. From the mouth of Marlon Brando. "I couldda been a contender. I couldda been someone instead of a bum which is what I am". Could have been versus might have been? I'd always opt for COULD rather than MIGHT. Did I answer your question Walt? Hopefully I did. If not I can talk some more! :)

Okay.
I think I get your intent, now.
"Might" has less probability than "could".

It's hard to tell if I prevented any good "could have been".

Maybe my divorce counts.  It "could have been" a good marriage.  Then again, it "could have been" a worse situation than ending as friends.

Maybe choosing not to go into computer programming in the 1980s count.  I "could have" earned more money.  On the other hand, I "could have" been one of those who sold "too early" to Microsoft and be kicking myself now.  LOL

I know m'dear. "Could" could drive a person crazy. I think any time you end up as friends no matter what the relationship was that no longer  exists is a very big GOOD. As for computer programming...would it have been your cuppa tea? I know nothing about it Walt but it SEEMS very boring to me. Dry. Right/Wrong. In/Out. Gray gray gray all day all the way. Vanilla ice cream. The taste is great at first. But five months later on a straight diet of vanilla ice cream? Oy vey. I couldn't do it! Now I am a retired Internal Auditor so my work world consisted of numbers. Some call us "bean counters" and think that is a very boring profession. But it was NEVER boring. It was always a quest to figure out what was wrong and figure out how to fix it. It's just that the medium was numbers. Different strokes. Thank you for your reply  Walt!  :)