Before broadband was widely available, TiVo used to purchase overnight paid programming slots across the US and broadcast modified PDF417 video streams that provided weekly program guide data for TiVo users. There's a sample of it on YouTube https://www.youtube.com/watch?v=VfUgT2YoPzI but they usually wrapped a 60-second commercial before and after the 28-minute broadcast of data. There was enough error correction in the data streams to allow proper processing even with less-than-perfect analog television reception.
A little less crazy and more straightforward (software on audio tape was super common after all): Radio stations and vinyl discs that transmitted programs to the microcomputers of the time (C64, TRS-80 etc.) have quite a long tradition. Some examples:
Not paid for programming but essentially the same tech: VHS games used to encode data in exotic ways so that the content was both viewable on regular TVs with a regular VHS player, but also had some kind of playable content.
Not quite paid programming, but Scientific Atlanta had a Broadcast File System that would send data to set top boxes over coax QAM channels used for digital TV. It would loop through all the content on the "carousel" repeatedly so all the boxes connected to that head end would eventually see the updates.
If I was to gamble I would say that Analog TV can store more data, compression algorithms usually work at say 1:200 compression ratio, they're extremely destructive, a raw 1080p60 in yuv420p is about 187MB/s, on the other hand a decent equivalent video on YouTube is about 1MB/s
