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RE: Wired or Wireless

I've broken a bunch of earbud leads getting them tangled in bike spokes, caught on bushes or just general wear and tear. Those nearly always break at the earpiece, so it's a matter of prying off the cover, making a note of the wire polarity, then shortening the cord, tying a new knot, scraping the insulation and soldering. Possibly more effort than $25 earbuds warrant, but it's a discontinued model that sounds OK and is a nice shape to insert, and the repair costs nothing.
Changing the jack on full-size headphones is easy in comparison, and you can upgrade to a nice Switchcraft or Neutrik 1/4" plug (or a pretty good Rean (Neutrik's cheaper line)), or perhaps change from 1/4" to 3.5 mm or vice versa. A $10 to $20 soldering iron kit, some 60-40 rosin core solder, and optionally stuff like heat shrink tubing, RTV (silicone) sealant to improve the strain relief. If this is beyond your technical comfort zone, look out for a "Repair Cafe" in your area, where someone will hopefully have tools and guide you through the repair.

There's a very good explanation of bluetooth audio on a blog somewhere. The most common BT audio mode, A2DP, can be OK if the bit rate is turned up to the maximum. But the default setting is far lower, and there's no practical way to tell what that rate is or to adjust it. IIRC the site links to an app that can modify the bit rate (but it wasn't compatible with any of my ancient devices). Worth trying if you've got hardware that's otherwise good, but impractical to upgrade (like an OEM car audio system). I'd hoped/assumed that the newer apt-X BT standard would be lossless, but reportedly it's not much better than full-bitrate A2DP. There's better versions of BT, and Sony has a genuine lossless protocol which some other brands/devices support.

Figuring out the capabilities of BT receiving devices is also cryptic: the best method seems to be to boot Linux, link up with the BT speaker or headphones, and then query the BT driver from the command prompt. (IIRC the site links to a suitable bootable Linux image.)

If you just want to listen to music without being encumbered by wires, consider lashing a tiny lossless player to the headphone band and plugging in with a very short cable.

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