As a very novice amateur, I agree that if the extra $250 for a spanking new digital scope is not a barrier over the $100 for a used analog in good condition, then the $250 is money well spent.
On the other hand, by choosing my sellers, I have two good 100MHz Kenwood scopes that worked out of the box. I did learn much from adjusting them per the service manuals. Earlier I bought one other scope for $50 that had a weak channel 2. Hoped it was in the preamp, but it is not and since I have 2 others, It is now not even a distraction. Shame, but....
I keep on my bench the Siglent and Kenwood. I like the Siglent because it can easily be put within reach, the Kenwood, not so much. But until I watched the Keysight videos linked toward the end of the post Charlotte started (
https://www.youtube.com/playlist?list=PL2XuMA5AwNUznkBE46tcZAF3p5Edxgm-z) I was always confused about how to manually set up my Siglent.
While I agree that a new digital scope (especially the new ones out this year) is something you can grow into (as my mother said when it came to shoes and pants), the learning curve is steeper. But the Keysight playlist goes a long way to making the climb easier.
Just my thoughts as a mature (maybe?) learner who is navigating all of this.