Decisions are never easy, and decision making is not one of my favorite things. Likely most of us would rather avoid making choices or decisions.
In the end, Squarespace won out for a variety of reasons. The following is based on my experience using WordPress, both free and self-hosted versions. I believe each of these platforms is structured to the unique needs of the individual or business owner making the choice between the two.
WordPress.com is free. Its self-hosted version, WordPress.org, is not. You have hosting fees, domain protections and registration, not all themes are free, and not all plugins are free. When you add all that up, Squarespace came out ahead.
It won't cost me much more to work with Squarespace than it did with WordPress. Plus I don't have to hire a web master or a host to keep me up and running. Squarespace takes care of that within my annual fee.
My biggest complaint with WordPress related most often to support. There were online forums where you could post your problem, and then hope for days someone would respond.
If you're not into coding or don't have funds to hire someone to maintain your site, Squarespace is your best option. Whenever I have needed support, the response time is usually within the work day, if not sooner. Not only are they responsive, the staff is knowledgeable, courteous, and extremely helpful.
Security probably should have been placed in the top spot. You may remember my post relating to my experience with hackers a few months ago. Someone else's fun hacking into my site created not only stress for me but a financial outlay I'd rather not have had to make.
With Squarespace, security is uppermost in the minds of its owners and technical staff. With your site, you have, at no charge to you, two SSL-related layers of protection. Squarespace also provides you free backup of your site content. However, this doesn't mean we as owners of our sites shouldn't take extra precautions to keep those files backed up as well.
Unless you're willing and able to pay a web designer, WordPress can cost you hours each month checking for updates to plugins and themes, watching for and resolving alerts for hacking and/or viruses, and sometimes just downtime. Downtime is generally based on the host you are using.
Since moving to Squarespace, I find that I have regained some of the hours spent with WordPress allowing me to write more and to have time to do other things I enjoy. And it's costing me nothing financially.
EASE OF USE IN BLOGGING
Preparing and editing a blog post is as simple as drag-and-drop. Having used the Elementor plugin in WordPress, I can say I find this much easier to use to create my posts and pages. If I have an idea or question about something I'd like to incorporate that isn't readily available or clear to me, a quick email or chat with support will help me get it done. (Support is available 24/7).
Moving from WordPress to Squarespace was next to seamless. A simple export process on the WordPress end to an import process at the Squarespace end, and everything except a bit of cleanup was done.
A word on the comment set up. I have not incorporated Disqus comments here for one reason and one reason only. When using Disqus on Squarespace, for some reason still unclear, I was unable to capture all the comments left for me on previous posts. Many of these were treasured comments for a variety of reasons. I realize that the necessity to login here and/or create another "account" may be bothersome for you. However, please note that you can leave a comment as a guest without creating an "account." If this becomes an insurmountable problem for many of you, I will reconsider my decision to not incorporate Disqus and determine a way to save those comments from the past, if I can.
I hope something here has been helpful to you, or at least explanatory in nature as it relates to my move. Please bring any inconveniences or errors you encounter to my attention. It is true two sets of eyes are better than one.