Are you pressing option-return (not cmd-return)? This is when you’re typing in the “With” column of the Text preferences. It definitely works because I just tried it again!
On Mac There is also aText which does everything I ever used in TE for a one off small payment. You can also use snippets in LaunchBar and assign them a quick shortcut
On iOS the tip about multiline has proved perfect apart from the dates thing, much appreciated.
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For me the macOS/iOS text substitutions work very well.
They sync across all my devices, are fast and are available without switching keyboards on iOS.
For more advanced snippets I use Keyboard Maestro on the Mac, and just don’t use them on iOS.
I find using the TE keyboard and expansion of advanced snippets on iOS is weird, ugly and time consuming, and I usually just end up typing the text myself (usually quicker)
All in all it has been solid for me, and I have not missed TE. 
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Thanks, I am on a perpetual ledge with this one: I don’t use expansion enough to make the issue clear. I don’t like the way TE keyboard works on Messages for example on ios; I like KM and I could just do with that but there is something about the way TE works as you say. If I were not on the ‘cheap’ legacy sub though I would drop it frankly. I don’t use expansions that much; not as much as I thought in fact. I could also put dates and snippets in Launchbar, I already use one or two. I found your experiment very interesting and helpful actually, though I have come to no real conclusion I feel a bit clarified… ?
Glad you find my experiment helpful. I have come to no real conclusion either, other than that it seems like it’s easier to keep using TextExpander – keep doing what I have been doing – and for $3+/mo. I can afford that.
But now I see why TextExpander ads keep focusing on the business collaboration uses. Because if someone were thinking about starting to use TE today, I’d ask them what they need that they can’t just do with Mac/iOS built-in tools.
Reminds me of something that happened 10 or so years ago. A friend who is 10 years older than me moved in to a new house and said he and his wife were not having a landline installed. This was the New Hot Thing, and I said to him, “We still have our landline. I feel old now.” He said, “Don’t feel old. You’ve been living in that house for years. It doesn’t make sense to switch of the landline and go to the bother of changing your number for everyone. But for us moving into a new house it doesn’t make sense to have it switched ON.”
And 10 years later I’ve stopped using the landline. My wife likes it for what turns out to be good and interesting technological reasons.
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That runs on iOS? Part of the objective…
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Nope, still doesn’t work. However, I was able to get what I wanted by using the “Text Substitutions.plist” trick, so I’m happy 
I was trying this exact same experiment. I think I am going back to Text Expander. The first issue is having to hit the space bar after the abbreviation to make it expand. I prefer how Text Expander automatically expands with the keystrokes and you don’t need to hit the space bar.
The second issue that I came across was when I updated to Mojave. For some reason, when I updated, my text snippets list on my Mac reverted back a list I had about 3 months ago. So I lost all my new snippets on the Mac. My iPad and iPhone still have the new text snippets I added. So now my Mac and iOS substitutions are out of sync - which was the whole point in the first place.
Frustrating to say the least. I still have 7 months left on my Text Expander subscription so I am just going to continue with that for now. Maybe I will look again in a few months. Plus, I got in early with Text Expander so I have the discounted subscription. Most my use cases for text expansion on iOS are with apps that work with Text Expander. The one big one that does not work is Mail. The solution for me has been to use Drafts for most all of my writing for emails.
I‘m coming to the conclusion that even though I‘ll keep TE (I‘m not on the subscription anyway), it’s a good idea to put some of the important snippets into the iOS/MacOS system, just to access them easier. Especially for email addresses etc. that are often used outside of texteditors like Drafts.
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Same here! Seems like a small thing but that was the straw that broke the camel’s back for me.
Same here. For me, the cost in time of researching and configuring alternatives is greater than the financial cost of continuing to pay for TE.
I don’t write a lot of email on iOS. Mostly just check “Froms:” and subject lines to see if there’s anything requiring immediate attention.
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I have made this switch for the past month or so and have to say it’s largely successful. For me the only thing I consistently miss is the date shortcut I made in TE. Every so often an app does not accept the system autocorrect and I need to expand in spotlight and paste the text in but otherwise it’s pretty good for my use!
If anyone knows how to do date shortcuts using native expansion lmk!
Heres a reason why needing a trailing space to expand can make sense. Let’s say I want to have an expansion rule for “TextExpander”, useful in threads like this, for instance. I can use “Te” as my rule. Hitting the space bar triggers it. If I had it triggered immediately I wouldn’t be able to write words like “Tell” as they would become “TextExpanderll” So to use the immediate expansion I would have to have the trigger be something that would not normally occur, like “;te”. So which is easier? Hitting a special character at the start or the space bar at the end?
See my post earlier in this thread about using Services. Experiment: Replacing TextExpander with MacOS/iOS text substitutions - #18 by tomalmy
I have all my snippets start with „x“ – easier to type than semicolon and rarely ever the beginning of an actual word.
Same here. I made the switch from a semicolon to “x” when TextExpander became available on iOS, so I wouldn’t have to switch keyboards to type my snippets.
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My system is to start a shortcut with a letter indicating what kind of text string follows. Primarily that’s “t” for twitter handle, “c” for company name. That’s followed by a q, then followed by the first few letters of the shortcut.
Thus, tqli results in @light_reading. cqmi results in “Microsoft Corp.,” and so on. I have dozens and dozens of those. When I run into a conflict when creating a new one, I edit the old one to add more letters until it becomes unique. Thus, if I encounter another company with a name starting in “mi” — say, “Minisoft” — then the Microsoft shortcut would become cqmic and Minisoft becomes cqmin.
(Is there even a company called “Minisoft”? Whatever.)
In practice, when it’s time to mention a company name for the first time in an article, I type cq and then start typing the company name until the full, proper name appears. And having to append a space at the end of the shortcut screws up that system.
And I oversimplified above. Actually what happens when I type a company shortcut is that I get a shortcode which, when entered into my company’s publishing system, produces the company’s full, formal name, with a link to the website and — in the case of publicly traded companies — its stock ticker symbol.
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I tried to do this as well, but my thumbs love to make typing inaccurate and I rely (almost to a fault) on autocorrect, so I have to toggle it when on iOS
On iOS, along with text replacements I’m using the new Shortcups app to retrieve the contents of a file stored on Dropbox, copy to clipboard, and then Ctrl-V to paste. Between these two solutions, I’ve had great luck replacing TextExpander.
Jim KY:USA
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PhraseExpress is just as powerful as TextExpander in my opinion, just another alternative to consider.