So, before I get too far into this post (or perhaps before I even start it), I should point out that there are essentially two recognizable types of WordPress. There’s the main one, WordPress.org, which is blogging software that you install on a hosting provider. You own it and manage it, so there are fewer restrictions, but there are more responsibilities. Then, there’s WordPress.com, a blogging service which offers you a free WordPress-powered blog with the option to purchase additional upgrades. Someone else manages it for you, so there are some restrictions, and additional features cost extra, but you don’t have to worry about anything (like features breaking, incompatibilities, downtime, etc). For a more in-depth analysis, please refer to this handy chart.
With the polite prodding of Mike Schroder over the years, I came back to my first-ever hosting provider, DreamHost. A lot has changed over the past nine years at DreamHost, all for the better. Resurrecting a nine-year-old dormant hosting account was no easy task, but Mika Epstein saved the day. It was like moving back into an old and much-loved home. Transferred a blog this size was rather rough and interrupted with frequent errors, but Michael Koenig of the WordPress.com Guided Transfer team had the magic touch and had my WordPress.com blog up and running on WordPress.org in a matter minutes. I don’t mean to sound like a commercial for one of our products, but the ability to sit back and let someone else who does this for a living (dozens of time a day) take charge of the whole situation is well worth the price.
There are a lot of handy built-in features on WordPress.com that are unfortunately left behind when you switch to WordPress.org, but it’s easy to either get them back or supplement them with something else. First, you’ll need Jetpack, which provides many of WordPress.com’s built-in features. Then, it’s just a matter of finding things to provide you with the security and reliability that WordPress.com is known for. Having talked with the folks behind Sucuri several times, I went with them for security. They’re good people, and you can trust them with the safety of your site. I also locked this down a bit more with a two-factor authentication plugin. Choosing what to use for reliable and automatic backups was an easy decision. I went with VaultPress, another Automattic product that’s well worth the price. Finally, you don’t have to worry about updates on WordPress.com, and you don’t have to on WordPress.org either, as long as you’re running the Automatic Updater plugin (from fellow Automattician Gary Pendergast).
In short, if you don’t like breaking things, stick to WordPress.com. If you want to experiment, WordPress.org is for you. DreamHost is great, and you’ll want to try Jetpack while securing everything with Sucuri, VaultPress, two-factor authentication, and the Automatic Updater plugin.