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"For free?"
On macOS, yes, using the macOS authoring tools.
On Windows, no, but you can buy one for a low price (I don't say what's the company name because they don't payment the advertise 
).
"But I have no idea how to do that on the Mac."
I would say that a web engine is your friend but that is so common answer I would say that Adobe AIR forums is your friend and you will got the "recipe" as you wish.
"I will never touch the Command line (Terminal)"
So, it's a good time to start I also don't use terminal a lot each days but I have macOS sh files to do that for me. I put them with a shortcut on my touch bar with a pretty icon, lolol. At least my touch bar now have a meaning to exist 
"Is there a guide out there?"
For macOS, yes, it is. I don't recall where, so you will have to type on a search engine
For Windows, the same company that you can buy the certificate (at least the one I use), also provide a pretty windows form UI to do it.
"Also, how recently did you publish to the Mac Appstore? Things change pretty fast with software"
I did it years ago. For that exact reason, constant updates on my side and store bulling developers with constant rules changes, I decided to certify my Apps yes but release directly to my clients without the store in the middle
"I imagine that Apple would require you to use a proper paid Cert right?"
Already answered above.
"Is a DMG file the final output?"
It's a .app You can easily create a DMG with a pretty background natively with macOS tools (search it on a web engine) or you can easily find a free or commercial tool for that on Mac App Store but I prefer to use the macOS tools.
I'm divide with what you said.
Agree and disagree, lololol
- they know AIR has only been declining for the past few years.
True.
- they don't know HARMAN.
True. The very first time I heard about Harman, was here in the forum. However no ones know me. At least we should give a chance.
- HARMAN has no roadmaps/future plans announced.
True. This is the worst part. Seems however that there is a promise to show the roadmap soon.
- HARMAN is asking for money but has NOTHING to show for.
True. I never (I mean, ever) asked for money before show the product. This is totally wrong. However they got a product in the very worst scenario possible, so, the rules are not exactly the same and people were also became unconfortable for not know the price table.
- we have an alternative ready to go.
And you should. I'm tired of nonsense excuses. But each one knows his plan.
This is true, but don't tell the hardcore fanboys 
One even posted a spreadsheet a while ago with all the new features we got in 2018. In the fake information spreadsheet, he had "os updates" as features in order to show that tech was keep moving forward...
The 10k took under consideration the biggest facebook group (4.2k) so I doubled it to be generous . If 10% ends up paying, we have a concrete 1000 devs.
ps. 90% of our clients asked us to move to other platforms once the March release (it was supposed to be AIR33) was missed.
"This is true, but don't tell the hardcore fanboy"
Hehe, we have a few around here, indeed
1000 devs paying from the very beginning, nothing bad at all !
"ps. 90% of our clients asked us to move to other platforms once the March release"
And, if I may say, it's a good advice that you should take in to account, serious.
I first evaluate the options out there, than choose a few, learn how much I could, test small use cases, see the history and the community and finally come to only one option.
Any new dev that arrives and do exactly the same I did, will not choose AIR (and I'm not taking into account the price model).
But anyway, if they start with 1000 dev's, it's very, very good on my opinion.
Thank you buddy for that ray of light, lol.
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