This is a real problem. When I worked IT, our machine shop was encountering this problem ALL the time. A "Sony" CNC mill was basically useless because of obsolete electronics. Cost to retrofit was around $5K as I recall. CNC equipment is fantastic, but it isn't like a Bridgeport mill from the 1940s. If you need it, you need it - but if you don't: Avoid like the plague! Automobiles "don't".
I collect old sewing machines. Are they as easy/convenient to use as the new computerized wonders? Of course not. BUT - 100 years from now, my old machines will still be running if someone squirts some oil in their general direction every year or two - compared to the computerized wonders that will be obsolete in 5 years, unrepairable in 10, and broken in 15!