The more I checked out Squarespace, the more I was impressed with it, so I eventually took the plunge. So first, a quick look at what Squarespace does:
Squarespace starts off with one of dozens of customizable templates. From there, it's pretty easy to build, maintain, and customize beautiful pages. And emphasis is on that word "beautiful" - Squarespace is all about HUGE photos and graphics, making it a go-to choice for photographers, artists, or anyone with huge galleries of images to share. I don't fall into that category, but I am a fan of Squarespace's elegant web building tools and responsive customer service. This New York-based company is doing good work.
The learning curve is mild. My HTML experience is only from crappy web pages I used to make 13 years ago. But through working for a nonprofit with a Wordpress page these past two years, I've had to step up my Wordpress game significantly. So that experience at least helped me know what was going on when I came to Squarespace. For merging what I did know with the unique way Squarespace works, they offer tons of great Workshops, help forums, and a very responsive customer service team. I didn't (and still don't) know the first thing about CSS - so I appreciate all Squarespace does the dumb the entire thing down for me.
But that leads to my only criticism of Squarespace. There's a balance between ease of use and customization. And in their battle to create an easy to use solution - Squarespace loses on the customization side.
I often found my thought process going like this 1) How I picture the website in my mind + 2) What Squarespace allows you to do = 3) What the website actually looks like.
A few examples. I use the Five template for this site, a template that can feature unique header images on each page (one of the reasons I choose this template). Early in the process, I created a new page, uploaded a unique header image for that page - edited the height of the image and it's appearance - only to discover in horror that the header changes I made on this individual page were copied throughout EVERY page on the site. This is something that's common throughout Squarespace. You get to make one decision on different items - then you just have to live with it EVERYWHERE on the site. Some of this I can understand, one quick way to make a good website look terrible is to have things appearing totally different everywhere on the site. But it's still limiting.
The H1 made a certain quote on my homepage nice and big, but guess what, H1 is also used for Blog Post headings, and that same font size made the Blog post headings much too large. So I had to come up with a compromise size that worked for both.
Have a piece of text you want to highlight in yellow or red or strikethrough? Those options don't exist.
Want to have one sidebar for the blog and another sidebar for other pages - nope, you get just one, which means the blog gets the sidebar and everything else does not.
I could go on and on, but just know that you'll run into these limitations often, there will be compromises, and you'll have to work around them.
Having said that, obviously I thought well enough of Squarespace to build my site around it and sign-up. It's one of the most elegant products of its type that I've ever seen and I think it's well worth the money. But I do hope that whenever Squarespace 7 comes around - it comes with many more customization options.