I have the same issue, what I ended up doing is getting an extension cable for the tv/stereo that is coiled, then while it's like 4ft coiled, it uncoils/stretches to around 10ft. Mine gets tucked away beside the stereo when I'm not using headphones.
You'll want to make sure you can get the right ends directly on the extension cable depending on what you need. Mine is large headset plug to the 3.5mm plug and works great for my needs. I don't like using size converters if I don't have to :D
Now for the question about the "advanced" headset vs stereo, depends on your ears and tastes. When watching movies, I want the best surround I can get, so my stereo headphones are 5.1s and work great when I would use them out there. Now I have an understanding wife that doesn't care if I'm watching movies at 2AM with the surround sound on so don't need them LOL
And for the cost, I refuse to pay over $125 for a good pair of headphones, make sure you can at least try them on for fit/comfort or have a good return/exchange policy. A lot of headphone reviews are subjective because we're all different.