Thinking of migrating your older Squarespace sites to Squarespace 6? A cost-benefit analysis

I have been using Squarespace for a few years now to host the few websites that I maintain. Last July, Squarespace released the latest version of their software: Squarespace 6 (which I will refer to as ss6 from now on). While I mostly prefer the changes that have been made in ss6, I've put off migrating all of my sites. This is partly through laziness, but partly because I've been confused as to how the pricing differences with Squarespace 5 (ss5) will affect me.

Luckily, Squarespace has fantastic support, and so I emailed them and they revealed all. I thought that others, who are also thinking of migrating, might find their answers to my questions useful. My original email is below, and I've interspersed their answers. A brief summary follows that.

My email exchange:

Background

Currently I have one master Squarespace 5 (ss5) account, two Squarespace 5 sub-accounts, and one Squarespace 6 (ss6) account that — if I understand this correctly — remains free while connected to my master ss5 account. I also have plans to start a fifth Squarespace site and trying to decide whether to migrate any or all of them to ss6 is the cause of my confusion. So here are my questions:

Question 1

With the 15% discount I get for the three ss5 accounts, this currently costs me $25.50 per month (the ss6 account remains free). If I migrated all accounts to ss6, would this end up costing me a flat fee of $8 per month (standard accounts, billed annually) for each account? I.e. a total cost of $32 for the current accounts I own ($40 if I create a new ss6 account)? I haven't seen any mention of discounts for managing multiple ss6 accounts.

There are not any special discounts for multiple sites associated with the same email address. You will need to upgrade each account individually. Also when you pay for an annual account you pay for the whole year right away totaling to $96 per account

If you decide to go for monthly billing you will be paying $10 per month

You can refer here form more information on our paid plans: http://help.squarespace.com/customer/portal/articles/1257605

Question 2

Under ss6, I understand that all accounts can be tied to a single email address which is fine, but is all the billing centralized as well, or would this be 4 or 5 separate payments off of my credit card?

All of you accounts would be billed separately

Question 3

If I went ahead and migrated everything to ss6, I guess I'd have to start with my master account. So I assume that initially I'd create a new ss6 account (which would have to have a new name?) and then I would import the ss5 content to it and finally redirect my domain name to the new site. Once I have the new ss6 master account I could connect other ss6 accounts to it, but my one current ss6 account is tied to my ss5 master account. The question here is whether everything will be okay if I disconnect the current ss6 account from the master ss5 account and then reattach it to the new master ss6 account?

There is no such thing as a master account within V6. All Squarespace 6 sites are managed individually. You are, as mentioned earlier, able to have several sites associated with the same email address.

When you unlink your Squarespace 6 site from your old Squarespace 5 account it will now function as its own independent site. You will not need to link it to anything else

So the bottom line is that Squarespace 6 removes the concept of centralized billing for multiple accounts. So this also means no multiple account discount. Without that discount, ss6 sites are 50 cents cheaper per month than ss5 (assuming you pay for a year at a time). But, I currently have one free ss6 account which would no longer be free if I get rid of the ss5 sites.

So if I moved my three current ss5 sites to ss6, I'd end up with four ss6 sites which would work out to $32 per month...a ~25% increase on what I currently pay. Hmm, still not sure whether the extra features in Squarespace 6 will tempt me to switch.

A new home

Moving home is listed among the most stressful events that one can experience in a lifetime. I wonder if 'moving blogs' should be included in that list too?

My first forays into blogging were around the time that Apple had just launched a set of tools under the '.Mac' umbrella. These tools were a successor to an earlier suite called 'iTools' and were in turn succeeded by the ill-fated MobileMe service (Dan Moren provides a good overview of these early transitions).

Under iTools and .Mac, Apple provided a web-based tool called HomePage that allowed you to create simple websites. As I recall, it was painfully slow to use and not very flexible. In 2006, things improved somewhat as Apple released iWeb, a desktop application that was part of the iLife suite of tools and which let you create websites that could be hosted on your iDisk (though you could also publish to other hosts).

The iWeb application made it relatively easy to create various different styles of website, and included a dedicated template for blogs. I used iWeb for a long time — hosting several different blogs, and my own personal website — before realizing that there were many things you couldn't easily do with the service. Support for iDisk-hosted websites continued as Apple transitioned to MobileMe, but the life-support cable for this service is about to yanked out, with Apple wanting people to migrate to its free — but iWeb-incompatible — iCloud service. Support for any iDisk-hosted sites will expire on June 30th and presumably these sites — along with any other files you may still have on your iDisk — will simply disappear.

Even before Apple announced iCloud, I had already been looking around for a alternative service to use for simple blogging and had started to use Posterous. Late last year, Posterous undertook some rebranding and became 'Posterous Spaces' with more of an emphasis on sharing and becoming a social network in its own right. This concerned me a little bit as I felt that Posterous's strength was in its simplicity, and Posterous Spaces seemed to suffer from a lack of focus. Further alarm bells rang earlier this year Posterous announced that they had been bought by Twitter. Although they claim that the service will "remain up and running", I'm now concerned that I can't count on Posterous as a long-term blogging solution.

All of which brings me — the writer — and you — the reader — to Squarespace. I've been hearing a lot about this company from many of the 5by5 podcasts that I listen to. For a low monthly fee, Squarespace will let you build beautiful websites to meet any need you have. So I'm now using Squarespace to host both my main website and my blog. It's been a useful opportunity to remove a lot of old content and try to give my website a much cleaner look. I'm still debating whether I should let all of my earlier blog posts remain on Posterous, or whether I should try to migrate them all to this site. In any case I'm really happy with the Squarespace service and hope to stay here for many years to come.