For me, it's not clear how Squarespace will be able to grow if their market is mom-and-pop shops. There are better economies of scale in targeting 1 enterprise accounts over 10 consumer accounts.
1. Support (fielding calls, answering emails, etc)
2. Updates (copy, design, patching)
3. Admin (billing, contracts)
And that's just off the top of my head. Having a client is rarely about just handling the hosting. You effectively become a technical resource and field all the duties that entails.
If you are on something that can't get hacked (static site) it is because you are a developer or at least pretty technical and the ease of use doesn't apply to you.
Again, this is all targeted at US (West Coast to be specific) SMB.
If hacked sites were really that much of an issue, then WP wouldn't be as popular as it is for business sites.
In any case, if you have a mature website, it's going to be complicated to switch from WP to Squarespace and vice versa. But with WP you still have the flexibility to host wherever you want, on whatever you want.
For backup, I either end up paying as much as Squarespace (WPEngine) or have to keep an eye on it to make sure its working.
I have no global stats on Wordpress hacks, of the clients I have running it (40???) I think probably 10 have been hacked. Zero have been hacked since moving to WPEngine (which is the first thing we do when we take over management), which is certainly something.
I'm not sure what the exact definition of mature website is, but I'm not sure it is that difficult. Certainly if you have 100s of pages, posts, articles etc. then it could / would take a while to make the move. At that point we're just talking about target market. Most of my clients have stopped posting tons of news / blogs because they were only doing it for SEO and it didn't really work anymore. In my world where sites have 25 pages with semi-limited complexity it just doesn't take long to move anymore.
I do certainly have clients with more complicated needs (member areas, ecommerce, etc.) but most of the time I just recommend they link out to that content and use another service (client portal in their main line of business app, shopify, etc.) rather than building it into their site.
Business owners have no idea how often they get hacked. They get hacked because business owners want a DIY approach and start installing plugins willy nilly without sandboxing and testing them, making their sites vulnerable to attack
September 2020:
Millions of WordPress sites are being probed and attacked with recent plugin bug
The sudden spike in attacks happened after hackers discovered and started exploiting a zero-day vulnerability in "File Manager," a popular WordPress plugin installed on more than 700,000 sites.
https://www.zdnet.com/article/millions-of-wordpress-sites-ar...
That's a hell of a vector for a hacker. Target one plugin - hit over 700K machines? Unreal.
You're not going to have any support with that though and lacking the CMS part of it, and if you want to use any of the more advanced features like Ecommerce then you're going to have to spend a while building that.
$5/yr for a whole site is simply not worth even talking about. It's not relevant.
The main caveat is that theoretically your costs could spike for some reason given you're paying based on usage. But if you're not doing anything complicated, I consider that pretty low odds.
I'm cheap when it comes to spending money on tech. I'm glad people are questioning the price.
We need more competition. It seems like we are just giving into the bigger companies, and I don't see the innovation I saw a few years ago.
(Fwiw I tried squarespace and found the UX awful)