We all know H-F sells cheap import tools, but some of them are pretty good.
I have:
5 speed 5/8 tapered chuck heavy duty bench top drill press I got in 1981 & it still works fine.
5 h.p. 60 gal 2 stage air compressor bought in June of 1986. Used almost every day, the only thing I've had to replace is the pressure switch. Still has the original belt, oil has been changed 4 times. I think it was around $800.
14" cutoff saw I bought in '91 for $50 to build one racecar. It built 6 racecars from; 91-96 and still works fine.
These are the major tools I can think of but I'm sure I have quite a few smaller tools that are fairly old & still work.
I've got the 500 amp battery load tester for $50. I bought it to replace a MAC tools one that looks just like it. The MAC version cost $250 - 25 years ago & the H-F actually works better than the MAC. Don't know how long it will last but I wouldn't be surprised if it outlasts me.
H-F has been very good to me. When you get a crappy tool they take it back with no hassle.
Back in Feb., myself & 2 friends went together & bought the 1000 lb. motorcycle lift. I had a coupon to get it for $280 so we each kicked in $100. the very next month they raised the price on the lift to $500.
I did some work for my friends (valve adjustment on a C50 & clean & rejet carbs on a Hyusong 650) & they gave me their share in the lift so now I own it. They know as long as I have it they can use it whenever they want any way.

What's your oldest H-F tool?