OP here. I'll try to answer everybody's questions. In a white collar office it would be unheard of for an employee to be expected to supply their own computer or stapler, but in the blue collar skilled tradesman world it's pretty common, maybe even happens more often than not. A guy doesn't like the equipment supplied, or there is no equipment supplied of the type he needs to do his job, so he uses his own tools, which can sometimes be high dollar. Mechanics do this a lot too. The machine I mentioned that we use every day, is a milling machine, which is used to cut and shape metal. The machine offered to me for sale is a piece of testing equipment, which doesn't meet the latest European standards, so isn't useful to the company any more because they can't use it for big corporate contracts, but it would be very useful for a guy wanting to do some work on the side for himself. Obviously as a traditional catholic, money isn't growing on trees so being offered something at better than half price is very tempting. I can't come out and ask if he has the moral right to sell me this, because that's just not the kind of thing you can ask your boss, if you want to continue to work somewhere. He also might not know himself because he inherited the business from his brother, who is also dead.
I asked a couple of guys about the tools. Everyone is pretty sure the milling machine (that's the $4500 one) did belong to the dead employee. As for the other tool, the one that directly concerns me, one guy thinks it belonged to the dead man, one guy didn't know at all where it came from. (But he's 84 and I don't think his memory is what it used to be. He's worked here for 25 years though so might be expected to know.) I'm personally now inclined to just buy it and not worry. Its a good deal, and the same rumor mill that said that these started out as the employees personal property also says that his widow was very well off and planned to travel the world after he died, that he made over $100,000 a year and did a lot of successful speculation on the stock market, and nobody knew for sure if the widow knew about the tools, cared, or maybe the boss bought them off her or she just let the matter drop since evidently his death took place several states away. So why assume the worst? After 7 years it's pretty clear nobody is going to come looking for them, the people who knew for sure may well be dead, and if I bought the one, it could do some good.
Sorry for writing a book lol. To sum up: Sometimes in machine shops employees bring their own tools to work. I don't want to ask my boss if he's sure the machine didn't rightfully belong to dead employee's heirs, because that obviously implies that I don't trust him or can come off as an accusation, but I asked around and nobody knows for sure, and it seems that probably the only people who know for sure are dead. So why assume the worst of my boss?