One thing you’ll see on every host that offers WordPress is claims about how secure they are, however they don’t put their money where their mouth is. When you dig deeper, if your site actually gets hacked they’ll hit you with remediation fees that can go from hundreds to thousands of dollars.
They may try to sell you a security plan that for example at Godaddy goes from $300 to $700 a year on top of your hosting. (Don’t be fooled by the low entry price, look at renewal.) It’s heartbreaking to hear stories of non-technical people forced into these high fees to fix something their host should have prevented in the first place.
When a host is powered by WP.cloud, it doesn’t need to do this because hacks are so incredibly rare. (That’s why it may appear more expensive, but the total cost of ownership or being a WP.cloud-powered host is much lower when you factor in human time.)
One problem we’ve had on WordPress.com is we do all these amazing things and don’t tell anyone about it, something we’re trying to change with our focus this year on developers and developer tooling. One great example is we’re so confident about our security, if your site gets hacked we’ll fix it for free! We’ve actually been doing this for the better part of a decade, just never mentioned it anywhere.
Pressable (which is WP.cloud-powered) does a better job talking about these things and has a nice landing page on malware cleaning and hack recovery that says essentially the same thing.
WordPress has done a ton over the years to move the hosting industry around upgrading PHP and MySQL, PHP extensions, free SSL, and in general using our clout to advocate for user rights and freedoms from even the largest hosting companies, and I’m proud to say there are a good number, for example the ones you see at WordCamps, that have not just embraced these values but actually been more commercially successful as they’ve done so. I hope security and auto-upgrades not just for core but for plugins and themes becomes the next standard. (Jetpack does this for free, some hosts charge $100/yr per site.)