If you need to test modern stuff like 5G or something, using old instruments would make it very hard work if not impossible. New instruments have built in "personalities" that enable "one button press" measurements to test compliance with modern standards.
But I don't need that for my ham radio and radio astronomy hobbies. For that, my stack of old instruments from the 80's serves me very well. They are "just enough digital": they do calibration and error corrections, and can be computer controlled via HP-IB, but no windows virus gardens and similar.
For example, some five years ago I bought a HP8593E with the 26GHz option for 1200 euros. I don't think there is a modern alternative that would fit that budget.
I do have a nanoVNA and a SAA-2, also a tiny SA ultra, these are great when out in the field. But when at home, I prefer to use my HP8714ES and HP8720A, the user interface is just soooo much friendlier.
My HP8663 opt 103 is bulky and heavy, bought it for 600 euros. Even today, it is still among the cleanest signal generators. Also have an HP8673 up to 26GHz, don't know of any cheap modern alternative.
I cobbled together a HP3048 system with HP11848 and HP11729. It is run by a DOS/ISA computer, is slow and bulky, but it measures up to 18GHz and gives great results.
My HP8970 uses totally obsolete detector based technology, but measures noise figures very well, on par with modern equipment.
Admittedly, I am an old fart, I used these boxes as a young professional in the 80's, so they grew close to my heart. But I do believe they can still be very useful today. Service manuals, schematics and even EPROM firmware files for most of them are available on the web, also the through hole components make them easy to repair (for now, I mostly had to replace some electrolytic caps).
Some of my instruments were old stuff even in the 80's, like the HP3400, which I call a "true-true-RMS meter", and I still find it useful.
As far as scopes go, I just bought a rigol 814 and a set of "pc bite" self supporting probes, it is great for debugging serial stuff. But when just needing to see some signals, for example in the audio range, I still sometimes fire up my tek 2232 (and 2467 until the battery went bad and it forgot it's calibrations).