At least part of the issue is I memorized tons of rules from AD&D 1e and 3/3.5e.
For 5e, I get it enough to play, but not to DM it accurately without having to look things up. And 5.24 throws in doubt what I know of 5e. New editions = new cognitive load from a changed UI.
Edition changes typically annoy me - feels like a waste of my time to learn yet another variant, and another sundering of the D&D community. Oddly, I was enthusiastic for 4e - I went to the launch party - but it’s now my least favorite variant.
Maybe WotC going to a subscription digital model could get them off reprinting “new and improved” rule sets. 5e is probably good enough to be a forever edition.
I like 5E, it's my favorite edition so far with 3.5 a close second even if I still have my S&P inspired barbarian from 2E. But 3.5 is second because it just stopped working after about level 14 or so. If there was an optimized caster running around, they just annihilated everything. For that matter, up until 14th level or so my martial characters tended to be far more effective than most even though I didn't really set out to make them that way.
Having said that though 5E could use a tune-up, after 10 years a lot of lessons have been learned. It's time for a refresh. But, as you said, a steady stream of income from DDB, VTT, or whatever could ease the pressure off of making another release for a long time.