First my parents both died in the same year. Then much later, two of my
longtime journeyman thieves died a few years apart, then a couple of
years later my wife of over twenty five years died, leaving me with a
bunch of businesses and property to deal with. And I felt such sadness
that I couldn't finish the game

I'm sorry to hear that... I hope if you care to pick this game up again, you'll have more luck with your relatives and professionals!

It gets really bad when you're running like 8 businesses.
I've had like 5 employees die in one year, followed by 3 more the next...
Of course, the character I'm running right now is 3rd generation now, runs 3 entertainers camps, 3 robbers dens, and a thieves guild, and used to run a quarry (2nd gen).
.. I'm really not sure there IS a finishing to it. :)

A finishing to what? The game? Nope, there is none (from what I've learned). To your expansion, maybe, as the city has its limits.
BTW, do you imply your current char has inherited the quarry? How did you do that? Quarries are rented, and once the one who got it on the auction dies, they are supposed to go back into the town's ownership.
(Or did you get it again with your current char?)

Ah, I see; I thought by (2nd gen) you meant you have had the quarry since your family's 2nd generation.

Thanks for your comments. I appreciated them. But truthfully I still have not gotten used to all the dying, but I'm sure I will eventually.
It's just a great game. I'm disabled so I have lots of free time, and lots of other things to keep me busy, but I cannot stop playing this game.

The Guild is basically nothing more than legalized crack in a digital form. As soon as you accept this fact, your life will be a lot easier...

lol alot of pepole seem to imerse them self a little to far. there was this guy saying hes son had no potential and his daughter was the only one with it lol.