I think my first blog was hosted with Blogger. From there, I moved to Tumbler, to Posterous and then to Wordpress,com. I switched between the four a few times, and then finally settled on a Wordpress.org hosted blog. That went well for a year or so, before I got tired of constantly having to update everything: the blogging platform. The theme. The plugins for the theme. The blogging platform. The plugins. The theme. At one point, a Squarespace subscription started to look really good, but I wasn't ready to fork over the money quite yet. I said, that's it, and went back to Wordpress.com. Over there, I was frustrated with the limit of good looking themes, and how little I was allowed to change them. Finally I gave up and went with Squarespace - which I should have done from the start. I fell in love during the two week trial and I haven't looked back. (Seriously. I haven't even deleted the other blogs. Who knows where they are right now.)
No, my troubles weren't over. I still had to scramble to modify a theme just to my liking. It's never easy, when you're picky like me, and you don't have any clue about programming or html or css or the likes. But somehow, with the help of other Squarespace users via their help site, I managed to tweak one particular theme, and the result really turned out well. Once you figure it out (!!!), the Squarespace platform is a treat to work with. I can use it from home, or at the office... anywhere I have internet. I can post from my phone, or even via email. The customer service is really, REALLY great. When until recently links from my blog wouldn't play well with the "thumbnail" function of G+, I emailed them and they didn't rest until they had fixed it for me.
Sure. Wordpress is awesome. But you don't get anyone to fix anything for you. After paying for hosting your website, you have to maintain its innards all by yourself. Squarespace is only more expensive, but for that little bit extra I get extra fresh service.