Out of curiosity; why?
My guess… because both are great until they’re not and then they’re a pain.
Drobos are brilliant until they break and the only solution is another Drobo. This compares to other NAS units that use standard RAID schemes. And from what I have heard from friends who use them, they do go bang eventually.
Squarespace is also brilliant — I used it myself for a while and I was very impressed. But… as soon as you find something it can’t do, you’re just plain out of luck. In my case it was “embed a Flickr image” which (at the time, don’t know about now) was simply impossible without going into developer mode. The other downside to Sqaurespace is cost. 10 bucks or whatever it is now is good enough value for a web site with that kind of power behind it, but I wanted to run three separate web sites on three domains. That triples the cost and then it’s not worth it, especially compared to a shared hosting plan. It’s swings and roundabouts for sure, as there is a lot more work to self hosting, but it gets expensive real fast if you have many sites to run.
One thing Squarespace does better than Drobo is getting your data out. When I quit it to return to Wordpress, I was able to get the bulk of my content out easily.
If you are into coding, Gatsby is a nice framework and has good blogging starters which you can use out of the box. Generates static html and uses markdown for the blog content. Use any markdown editor you like to write a post. You could use some tools and automations to reduce the manual work. Or Ghost is also great without any coding.
I know im late to the party here but while everyone has offered up many niche/bespoke solutions, there is one downside of not using something with some marketshare and that is… “is it going to be around tomorrow?”
Its pretty save to say Squarespace and Wordpress for example are gonna be around tomorrow and the following years. Some of these others who knows. I hate that uncertainty. Especially if I am going to put a lot of work into something.
food for thought.
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After reviewing the many good suggestions, at the end of the day I decided to stay with Squarespace. Working around the mobile inefficiencies are easier than changing platforms. 
Thanks everyone for the great advice and help!
Agreed, but I took a leap of faith and went with micro.blog anyway. I figure blogs are ephemeral. I’ve started and abandoned many.
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Well I for one expect mine to be timeless classics. 
My blog is run off of Wordpress.com and is really easy to use on iPad. I set the whole thing up from there and it was really easy.
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have you written somewhere your thoughts on why you went with Micro.blog?
I also considered them for my blog and at $5 a month (which includes hosting), its great value and is also run by great people. I went with Ghost because of Ulysses had built in support for Ghost and the cost was only $6 a month. I am cross posting on micro.blog though
I am by no means switching as @Bmosbacker rightly said that its best to work around inefficiencies than change platforms. Plus I do not have the technical expertise to deal with a platform change. I am trying to keep my blog as nimble as possible.
Anyway, its interesting to read about what considerations were made when selecting a platform.
I like Ghost. It’s a shame they moved way upmarket within a year of launch and their own hosting starts at $29/month.
But you can get cheaper Ghost hosting (though I can’t speak to uptime, speed, etc). Ghosty.host starts at $2/month for barebones shared hosting, and their premium plans are still cheap at $4 and $6/month.
If you just need to throw up static pages, and you have space on even a free Dropbox account, I think Blot.im rocks at $4/month - it’s dead simply and you just toss files into a Dropbox subfolder on your Mac and Robert’s your parent’s sibling. If you want network effects for strangers to find your blog the cheapest options are Tumblr and Medium, but my favorite is still Wordpress-hosted blogs at wordpress.com (with hashtagged crossposts linking back on FB/Insta/Twitter).
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That’s a start. Also, it’s dead simple. Wordpress has turned too complex.
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One of the features of Ulysses I appreciate is being able to upload posts onto my WP driven site. Text and rought placement of pictures sent from Ulysses then polishing with one WP editors (I still use Classic not Block.)
FYI unless micro.blog changed its policy, you can have a micro.blog for free if you post from your own blog (or anything that sends out an RSS feed). I remember that many users playing with micro.blog when it started up simply created a WordPress site specifically for that purpose, posted to it just like any other blog, and since the native micro.blog clients for iOS and Mac interface directly with the WordPress blog, when using them to post it looks just like using a Twitter client(although you can also use any Micropub or WordPress client to post to the Wordpress blog as well).
But Micro.blog is a little too ‘dead simple’ - you couldn’t even post videos there until a year ago. 
Some of the limitations are inherent in the design. As Manton Reece, creator of Micro.blog noted:
Micro.blog doesn’t have hashtags, trending topics, or retweets because I think the focus on those features in other social networks has led to people being exposed to harassment, hateful posts, and even fake news. For Micro.blog, it’s more difficult to accidentally stumble on a random post unless it’s part of a conversation you’re in or from a section that is actively curated.
This was an important design decision and we’re not walking away
So while micro.blog is very simple, that simplicity keeps people from finding and engaging with individual blogs and posts.
Wordpress-hosted Wordpress is actually quite easy to use (I have a 75-year-old technophobe neighbor using it to post about local goings on), it has dozens of polished free templates, and is a lot more powerful (if you want things like comments, forms, Yelp reviews, maps, and more) if desired. With Microblogging templates on Wordpress (which I remember discussing with you in 2018) you get the best of both worlds.
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This is great value and it helps Ghost can be hosted elsewhere. Never heard of Ghosty before.
I agree if Ghost had cheaper plans, I would have hosted with Ghost and not worry about it.
I am currently using Digital Ocean with Ghost. I also considered Blot but I didnt want to deal with Dropbox now that i am all in on iCloud. I wrote about it here: How to frugally start a website?
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I may migrate back to Wordpress at some point. I enjoy fiddling with blogging and trying different things.
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I believe Blot can now just use github instead of dropbox if you choose.
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I need to look into Github. I thought the free tier didn’t include private repositories but maybe I was wrong about that, or maybe they added that after the Microsoft acquisition…
They have added free private repositories
Blot can use Git instead of Dropbox. Git is the underlying technology Github uses, but they aren’t the same thing:
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Yes, that’s what I meant. For me private repos were the one reason to consider Gitlab over Github (though I never did). Now I could see myself using Github for some things.
But Github’s limitations in its free plan (250Mb, 2,000 Actions minutes/month) would still have me choose the free 2Gb Dropbox plan for hosting Blot files, just for the flexibility to host video without worry. (Of course, the free Wordpress.com plan comes with 3Gb storage, so I’d probably still favor it overall.)