Thinking again about moving over to SquareSpace 6

Regular readers will know that my site is hosted by SquareSpace and that I am using the SquareSpace 5 model. These readers will also know that I have looked at moving my site over to the new SquareSpace 6 model that SquareSpace introduced late last year.

The three biggest upsides to converting over to SquareSpace 6 are:

• A much wider posting width—I would have 900 pixels of posting width, and possibly more depending how I set the site up; this is compared to 650 pixels of posting width now.
• The site would would work much better for mobile users and I can see from my browsing statistics that about a third of my readers are now visiting the site using a ‘mobile’ device (basically meaning either a tablet or smartphone).
• Better automated handling of photographs with galleries, with lightbox viewing, and with automated resizing to fit the viewing device.

The main downsides to moving to SquareSpace 6 are:

• I will no longer be able to use Microsoft’s Live Writer to pre-key my posts.
• When I transfer my current content over from SquareSpace 5 to SquareSpace 6 the precise formatting will be corrupted/lost—I would have to restructure every post after the transfer, or ‘not care’ and just leave them however they get transferred.
• From what I can work out my tagging will not transfer over which will mean that I will have to do it all again—if I want to continue tagging posts.

None of these are trivial issues but the biggest issue is the first one: Not being able to use Microsoft Live Writer to pre-key my posts. I could key the text up in something like OneNote but the part I would not have is the ability to position and size images precisely how I want them—which is one of the amazing things Live Writer lets you do.

Is there anyone out there who has moved from SquareSpace 5 to SquareSpace 6 that has any suggestions or thoughts about this? I really am confused about what to do.