There are many people who can't imagine relying on an analog Tektronix scope; it's not even digital! It does depend a lot on what you're doing, of course, and there are many people who *do* rely on them. I prefer my 485 as daily driver, unless or until there is some feature I need on the cheap digital scope.
As to the fear of the unknown... you'd want to try and get as good a sense as possible of how well it's working before you buy, though there is always risk. I have a couple that were in great shape, and a couple that need work. The nice thing about it is the manuals are readily available and amazingly helpful. And while there may be obscure parts that fail, my guess is that you'd mostly need standard things like... capacitors. Plus there is a helpful community of experience out there. And videos. IOW, my view is once again "don't be scared." :-)
I also very firmly believe that your projects in your bench will tell you when it's time to get more gear, as opposed to trying to predict the future and what you might need someday. This is not necessarily a popular view, and doesn't always line up well with the Joy of Acquisition of New Shiny Baubles!