It all kinda depends on what you do, what your hobbies are, do you do a lot of one off work, etc... Someone mentioned brake rivet presses earlier - if you own a model T (where you have to replace transmission bands every so often) or work on old stuff, that would be a godsend. (I had one, my dad borrowed it, he passed on, his 3rd wife's kids, not knowing what they had sold it for $25)...
For me, things like a Bridgeport Knee Mill, a good lathe, etc, are a blessing... because I work on old ****, so you end up having to make one off parts. IF you make production quantities, then yeah, that "****" is so outdated it costs you m ore in individual set up time than your time is worth. If you make, fer instance, valve spring retainers for 1920's Maxwells, then hell yes, you NEED tools like these because (a) no one makes them, (b) programming a CNC to make 3 would take longer than just doing it, and (c) the demand for these are, other than (us) idiots who rebuild/restore ancient mechanical stuff, damned near nil.
On one of my old car sites, someone was bitching because no one anywhere has a certain widget to replace a broken part. IF you have the old school manual machines, then you can make them at a cost of damned near nothing other than time, materials, and maybe heat treating.... you can make the parts you need (and maybe a few extras for friends) and go on with your life. If I wanted to, say, machine a bushing for a dual overhead Miller head from the 1920's, well, you either make it or you spend a ton to have someone make it for you.
Me? I would damned near DIE for a good Bridgeport and Hardinge toolroom lathe and an annealing oven that is 5º or better accurate.... People tend to (or have to) "make do", and I'm not saying there aren't good people out there making quality repop stuff.... but there's a lot more who got to the point of "It won't run more than 1000 miles, so no one will notice"....
So... because, well, yeah, I make it, I KNOW that the quality level is 110%. I've spent good, hard earned money for stuff I KNOW (and have tested as such) is MAYBE 50% of an original... I can make one at or better than original, but for lack of the "toys" to make it.