I guess by awkward I probably mean soul destroying and painful.Awkward to develop? It's super easy, 10x times easier than any other framework. Some years ago I was very rusty and thanks to WP I went back to the programming zone.
The only issue, as it has been already stated, is the vulnerabilities and the huge maintenance it requires if you use it fast and furious.
I've had sites self-developed up and running for 10+years even with an obsolete PHP 5.2 and without any single bit of maintenance without issues.
But WP as soon as you stop updating plugin specially the famous ones, a vulnerability appers, and you have it hacked in a couple of weeks.
On the other side, I have updated sites with 12 years based on WP to the latest version without a hassle, but those pages self-developed ages ago, have been turned officially deprecated, because I don't have the time to update that massive amount of code anymore
So basically, nowadays for 9 out of 10 scenarios I may choose Wordpress. 50% of the internet is based on WP and is for a reason.
It's a mess, or at least it was. Having said that, on the user side it just worked and that's why it's popular IMHO.
The security stuff alone is enough to make me stay away on its own, though.
I think the caching plugins are smart, that's one thing I'd say but that really should be a core feature for users that can't (shared hosts) or don't know how to set up a web server.