I've had, similar to most people here, some of both!
One of the dumb ones, I bought not once, but TWICE! It seems I didn't learn.
That item was an "inexpensive" outboard automation system. The first one was by J.L. Cooper, and was one of the first "new" midi devices. I bought the thing to automate a mix on the old SpectraSonics board at Ardent Studio A in about '85-'86. Nothing reasonable, of course, was made to retrofit to that console. Once it came, there was a massive amount of cabling to be made, at great expense. Then a massive amount of patching, and a steep learning curve for the way it worked. Then it wouldn't. (Work, that is.) I tried and tried. Ended up just sending it back to the dealer in hopes they could sell it used. Which they never did.
But then, about 9 years later, I tried again! Instead of spending $80-100k on one of the nice automation packages for my Neve V3, I decided to try out the Mackie one, for a single project. Same thing...stupid machine! A lot of cables and patching, and no real result. This one sort of worked, but it didn't sound good (all audio had to pass through it), and it was a lot more trouble than it was worth. That one's still sitting in my old useless gear storage room.
I finally learned there is no free lunch!
As far as good purchases, I will agree that you can never go wrong with high quality, classic gear. Any old Neumann mic, any excellent mic pre or other gear with a solid pedigree, has stood the tests of time and session.