Personally, I don't think the computer analogy holds up in regards to a CD player choice. Computers become "less usable" over time because the software becomes more complex and requires more CPU performance, memory space and disk space to run. A CD player that you buy today will still play future CDs with the same performance that it delivers today.
So, if you audition a CD player today and it sounds good, it will still sound that way in the future. Now, there may be better and less expensive players available in the future (like computers), but they won't make your player obsolete.
That said, I generally would not recommend buying most older CD/DVD players because they have a relatively high failure rate over time. The transport mech (motor and lazer assy) tend to fail after several years of use. Of course, if you find a great deal on a player and can budget in the cost of a replacement transport mech, go for it.
What is your budget for a new player? Knowing this can help forks offer some suggestions.
BTW, Cal Audio has been out of business for several years, so you would be exposed to parts and service availability if you purchased that unit.