4e's online tool was fantastic at the end. Like truly excellent. I get a lot of people didn't like 4e, but at the end of that run they had a very good, useful tool for use with that game.
5e's online tool is fantastic. DnDBeyond is an excellent set of tools.
D&D Insider was crap when it came out. I think 4e was mechanically extremely strong, I own most of 4E D&D products, but it didn't feel like D&D
to our group and we never got interest/motivated in playing/DMing it. This is not a poke at the 4e edition. I never touched D&D Insider at the end, but that doesn't negate the fact that D&D Insider isn't around anymore. Anything you put in there (money/time/effort) is gone.
DDB is like Windows, you want to play your favorite game, your stuck with that ecosystem. Only recently did WotC open up D&D to other VTTs (like Foundry) I think Roll20 also had official D&D options a for a while, but has the same issue that DDB has, it's a 'live' service. IF people had a choice, a LOT of people wouldn't choose DDB, just like a LOT of people wouldn't choose Windows if they weren't restricted to it... It's not unusable, certainly not 7 years after release. But when I went looking at the available tools (DDB/Roll20/etc.) I wasn't really impressed by them when I compare them to the stuff 3rd parties made during the 3e era, add to that the 'live' service model and what happened to official 3e and 4e tools, and I'll happily call it crap. Maybe my standards/requirements are just unrealistically high or people have just been conditioned to accept the 'live' service and 'walled garden' models.
IF you're happy with DDB and how Insider wound up, be happy. Don't let me rain on your parade. But I said I was going to be harsh on WotC/Hasbro on their software/service products and my
opinion stands, just like yours. It's up to others to decide what they do with our opinions on the matter. Of course I might change my mind (just like you could), but WotC/Hasbro has been doing 'bad' things well into the 5e era, so there isn't much trust there that things will change for the better...
First off, everything I've purchased on DDB is available to me right now on my phone because you can download copies of anything you want, and I have. So it could shut down tonight and I would still have all of 5e and my third party content. So much for that hypothetical.
How long before that phone app goes EOL and no longer work, and does the app actually keep working if it can no longer phone home (every day/week/month/year)? Will you keep your phone OS on this version forever? Don't get me wrong, I can export DDB books in not approved ways, but that's just a crappy looking PDF. And that's just the text, what about the rest of the functionality?
With the VTT 'I shall not name again' I have just backed locally up every stable release they ever released. I can install it on any Linux/Nodejs (virtual) machine I want (and use a modern browser to connect to), I can also backup locally any module I've downloaded. Including the official D&D ones. I can also backup locally all the things/adventures I made. If in 20 years I want to run the things I have today, I can. AND I can play games on it that aren't D&D or even medieval fantasy...
But I also understand that this is not realistic for the average D&D player/DM to do, the moment they hear Linux and Nodejs, they run away screaming (I just run away screaming when I hear Nodejs*
)...