I guess you never have guests? Also a pair of headphones wont differ that much from a 2.1 system that'd I'd use that as an argument, it's all psychoacoustics mostly at that point.
Also, when talking about speakers, what upgrades? You don't need yearly upgrades with speakers, unlike with Apple headphones. In the past ten years, I've spent about 400 dollars for a pair of Yamaha studio monitors fit for professional audio use, certainly for light audio entertainment as well. They'll still take any Apple headphones through the ringer in terms of quality.
Also, when talking about speakers, what upgrades? You don't need yearly upgrades with speakers, unlike with Apple headphones. In the past ten years, I've spent about 400 dollars for a pair of Yamaha studio monitors fit for professional audio use, certainly for light audio entertainment as well. They'll still take any Apple headphones through the ringer in terms of quality.