Just to throw my 2 cents in on how I fixed mine. Regarding the issue of the orange light blinking 3 times - a few years back I think I resolved it by playing around with the charging/sync plug that goes into the 2nd gen shuffle. The plug pin itself had loose parts.
Recently it played up again and I wasn't unable to fix it, so I bought a replacement cable from eBay for $3 and now it works perfectly. I wonder if there was a production/design problem with some of these plugs as it seems to be a common issue with the 2g, although there could be many reasons for the failure.
The replacement plug does not have a silly cradle. If you're still having problems, then for a few dollars/pesos/pounds I think it is worth a shot! Long live the 2G Shuffle!! Good luck!
Been having the same problem with both our old Shuffles. I have a Windws8 laptop and have been struggling to get beyond the 3-flashes (although it does seem to charge the machines). Just plugged the shuffles into one of our netbooks (running Windows 7) and it charges fine. Very odd.....
Also, even though the shuffles don't seem to be charging (according to the lights or rather lack of) they are recognised by my laptop and I can sync them.