Well, to be honest, I’m not doing that as much anymore, for a couple reasons:
-
When I was doing it, we were on a heavily-metered Internet connection (20GB per month) and I wanted to make sure that I could download the video once and play it anywhere.
-
I’ve gotten into the habit of waiting as long until movies come out on Blu-Ray and then waiting until the price drops from its initial level (watching via https://camelcamelcamel.com). 99% of all Blu-Rays now come with a digital code, so I can stream them on my iOS devices/Apple TV, and I have the Blu-Ray which I can convert into a restriction-free MKV if I want to, but in practice I rarely do.
-
The app that I used NoteBurner M4V Converter Plus for Mac does not work on anything later than “macOS Sierra 10.12 and iTunes 12.8” which, at this point, means that I’d have to run the conversion on my 2007 iMac with 6GB of RAM… which is pretty darn slow. Which is a shame, because the app worked well, and even supported subtitles.
If I’ve purchased something via iTunes but not on Blu-Ray, I’m more inclined to check the back some of Internet trucks than try to deal with converting the iTunes file directly. For example, when Into the Spider-Verse came out, I bought it on iTunes the day that it was released. I wanted to take a screenshot of it, but the iPad won’t allow that… because piracy? 
Who TF knows… anyway, ~20 minutes later I had an MKV and took the screenshot in VLC on my Mac instead.
I also saw the movie 4 times in the theater and also bought it on Blu-Ray the day it came out, because sometimes I’m terrible at following my own advice. Of course it came with a digital code… which I no longer needed, because I had already bought it on iTunes… {can someone explain to me why movies come out on iTunes before Blu-Ray? I really don’t understand that at all, but it’s usually a 2-week delay, which seems ridiculously stupid. Then again, it’s Hollywood and technology, so I should expect stupidity, I suppose.} Anyway, I didn’t feel much guilt about acquiring a DRM-free version of a movie I’d paid for about 6 different times.
