Hi all,
First post here - like you all, I discovered this week that at some point between last winter and now, Apple shifted to HLS streams when "downloading" purchases from within the macOS TV app. Was going out of my mind trying to transfer some downloads to my Nano (yes, I still love that thing - less backlight in bed, keeps the "Too bright!" comments from the wife away) with everything erroring out ("...because it cannot be played on this iPod.").
But with some prior comments in this thread leading the way, it turns out that (at least in my case) it was still downloading in .m4v format in addition to the HLS file, thus needing to find a slightly backdoor method to getting these videos onto iPhone/iPod. Read on and see if any of this works for you.
To start, the first thing I noticed is to watch the download progress within the TV app - if you are seeing MB transferred along with the percent complete, it's downloading .m4v by default and the below may be irrelevant, i.e. easy transfer.
However, if only a percentage is being displayed, it's downloading with HLS and this convoluted method may apply.
My test was with "Back to the Future" - never had any problems with the download until this week. First thing I noticed was that it was only a percentage indicated in the download progress. Here are my current preferences for downloading (although I did test with a variety of options, all seemed to give the same results):
After the download completed, I wanted to see what the file itself looked like:
Turns out that when revealing in the Finder, I had two downloaded files in the target folder - see below, along with the Get Info detail for each:
If you have another Finder window open to the target device, dragging the .m4v file into that Finder window does start the transfer onto the device.
This may also work for those of you wishing to archive the actual .m4v file, as opposed to transferring onto a device for viewing.
Part of the problem, it seems, is with the TV app itself. When dragging a download to the device displayed in the TV sidebar, it seems that it defaults to selecting the HLS file behind the scenes, and not the .m4v, hence why nothing is being accepted as being playable.
Like I said - this may work for you.... but with Apple development falling by the wayside these days, any glimmer of hope helps.
The only caveat is that I'm still testing on recent movie purchases - currently downloading something I purchased a week or so ago. Will advise whether this method still holds.
Now if only I can find a way to get my new iPhone to actually MOUNT my purchased library (after close to a week of "Syncing your library...") - and that's for just Music. The TV library is a whole other headache...