I agree that it's hard, but they've shown the willingness to do hard and boring things before and take their time, launching in markets when they're ready (look at how long it took them to launch on Verizon).
However, the cable and sattelite providers also have a huge interest in pushing their own set-top boxes loaded with their streaming services etc. So I think the real issue isn't just software, it's politics and contract negotiations.
I don't think Apple is going to be happy with a situation where customer spend 90% of their time pushing buttons on a non-Apple remote control. So they probably won't be relying on set-top boxes unless they think they have such a compelling story on the content side that most people won't bother with the set-top box.