For the record, I've done D6 to D7 and D7 to D8 data migrations on fairly complex sites. I say "data migration" and not "upgrade" because you're effectively creating a new site, then migrating the data over. Essential modules in one Drupal version may not exist in the next, though I understand D8, 9 & 10 modules are near identical so upgrading is way easier.
There's another thing that really split the community, many want automatic security updates to Drupal core, but the Drupal core devs have taken a hard stance against this. Letting the site rewrite it's core files is seen as a major security risk, which I agree, but in my opinion that's outweighed by an even greater security risk. Every Drupal site needs an active dev to immediately perform security updates, but this isn't the case for half (or more) of Drupal sites and those sites get burned badly by the policy of forbidding automatic security updates. Drupal's adherence to "best security" has led to some absolute disasters (see Drupalgeddon parts 1, 2 & 3 where thousands and thousands of sites were hacked).
Regarding Drupal versus Wordpress comparisons. Drupal has been moving towards being a Content Management Framework that requires a knowledgeable PHP developer to build and maintain. If you want an easy way of creating a blog/website that practically runs itself and has thousands of plugins for just about any functionality you can imagine, you don't want Drupal, you want Wordpress.