I really liked to use vagrantup.com/ when I was still doing PHP on a daily basis. There's a great vagrant setup at vccw.cc
You could, actually, have the vagrant box automatically give you a ton of dummy data by running some key SQL scripts. Especially true if you find yourself consistently using the same sorts of custom post types.
As for remote db, yeah, you can totally do that if your remote server is set up to handle that interaction. I'm not sure how much direct control you have over the databases you work with.
Is Vagrant similar to Docker? I'd started looking into docker but haven't really gotten around to playing with it.
As far as server access, everything I'm working with is running on DigitalOcean droplets so I'd assume that means I have full control over the MySQL and the firewall between the two. Is there a recommended way to make that connection happen securely?
It is similar to Docker, but Vagrant is basically a wrapper for a vm. Docker is some kinda magic I don't fully understand yet, but if you have more experience with that, I'm sure you could do the same thing with a container.
Basically, you would open up your MySQL instance to remote connections and whitelist your own IP connection.
We're a place where coders share, stay up-to-date and grow their careers.
We strive for transparency and don't collect excess data.