In my case I must say that at least emotionally every piece of good analog equipment has been a good investment. I've been using DAWs for over 20 years and since the beginning of that time the promise has always been that it (the plugin, the DAW, the whatever) sounds like analog. In my experience this promise has never been fulfilled. No plugin sounds like a 1073, a 2254, a V76, a Cranesong. For me digital works great as a recording media and for tasks analog can't do. But contrary to the recent trend that even famous mix engineers go fully digital, I am actually working on using more analog devices in my DAW setup. I am even developing and building analog devices for that. For me it works better: it is more fun, sounds better and gets me better results faster.
Also the resale value of good analog equipment will hopefully still be good in the future. At least every good piece of analog equipment in working condition does still have a value. I wish I could sell all the plugins I have bought during the past two decades that I don't use any more...
Michael