Squarespace has what I consider an image management problem, at least when it comes to using images in blog posts. Inserting an "image block" into a post in order to display an image is relatively straightforward, but when it comes to choosing the image in that block, that's where the problem lies.
You see, oft times the image I want to use as the leading image for a blog post is an image I already have on my website in one of my existing galleries. However, as SP's image blocks work today, you can't simply point to an image in one of your galleries; no, you have to upload a new image. So that means, even though I have an image on my website already, and thus already taking up some of my allotted space, I have to re-upload that image separately into the image block if I want it displayed in my blog post. That's ridiculous! You should be able to point to the image files already on your website without having to duplicate it - hell, I could easily do that with a super-basic HTML-only website. But I can't do that with an advanced CMS like Squarespace? Again: ridiculous.
With slideshows, as I have displayed at the top of this post, there's a little more functionality, but there's still really less than there should be, in my opinion. For a slideshow, you can at least point to an existing gallery on your website; you don't have to upload new images. That's a big step in the right direction. If they gave us that same functionality for single images, I'd be relatively happy. However, one thing I'd like to see them implement is the "collection" functionality like you get on photography image-hosting web platforms like Zenfolio or SmugMug. On those platforms, you can create galleries that are really just collections of photos from other other galleries; that is, the photo isn't being duplicated in the new "gallery", but is simply pointing back to the photo in the original gallery. This makes it easy to create a collection of Fall photos (for example) that's really just collecting Fall photos from your other various landscape image galleries, and then present that collection as a slideshow in a blog post, on another custom webpage, etc. It's a really handy feature. I've been a Zenfolio customer for years, and I've really enjoyed that functionality.
Now, you might be thinking, "well, just use Zenfolio or Smugmug then; Squarespace isn't a photography site." I would get your point, but really, Squarespace markets itself heavily to visual artists, and to photographers in particular. Listen to any photo podcast or watch any photo vlog on YouTube, and Squarespace sponsorship is all over those things. I don't think you can find a single one that isn't sponsored by them! As such, I think these photo management touches should be a major focus for them. I don't really do photography professionally anymore, so I've been thinking it's time to finally turn the second, professional site off (it's already got a front page saying, "thanks for the memories; buh-bye"). I'm kind of debating whether the platform I stick with should be this Squarespace or my other Zenfolio site. My personal space has always been here, and yeah, there's a little more website customization flexibility overall with Squarespace, but... I still get a blog with Zenfolio, the templates are mostly good enough, and the use of my existing imagery within that blog is MUCH easier/better there than it is here. Considering most of my focus on my website is on my photography and I mostly use the existing images in my galleries for my blog posts, what's the argument to stick with Squarespace over Zen?
So Squarespace, I hope you're listening, as I really doubt I'm the only one that feels this way. These asks are actually pretty basic things to implement - one of your interns could probably code it. So please get with 2011 and get us this functionality already.
A frustrated photo blogger.