I guess a part of this is inconsistency between development environments as well, but generally speaking, while not completely impossible, the dev user experience is just that bit more fiddly.
For a prod server, the process can be as simple as (Ubuntu/Apache being a common setup):
apt-get install letsencrypt && certbot --apache
Or more generally:
$PKGMGR install certbot && certbot certonly
For dev, you need to either select and install an SSL library, generate snakeoil certs and install them into each vhost you use, and thereafter go through every varying and occasionally unsurpassable browser warnings about unverified certs, OR - much, much more complex - install and maintain a boulder setup.
Given the above, most devs will continue to take the chrome://flags easy way out, which doesn't really allow proper testing of a HTTPS setup locally.
