I just replaced both of the rear bearings on my '00 S. It was indeed the right rear that failed though. I replaced the left just while I was at it. It's not a bad job to do, but I had to buy the SIR tool for $260 from Pelican Parts to do it. With that tool it was not too difficult to press out the hub and bearings and then press the new bearing in and the hub back on. The right rear bearings had definitely dried out and were full of metal shavings. The car is MUCH quieter now.
Overall I paid $260 for the SIR tool, $30 for shipping, and $25 in tax - so that was spendy. The bearings were only $36 each though, total cost about $400 and I still keep the tool to use for the front bearings or on my 996.
The local independent shop wanted $600 just to remove the bearings and press in the new ones even if I brought them the wheel carrier!!! That was just insane as I was going to do 85% of the work. 
Kirk
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2000 Boxster S - Gemballa body kit, GT3 front bumper, JRZ coilovers, lower stress bars
2003 911 Carrera 4S - TechArt body kit, TechArt coilovers, HRE wheels
1986 911 Carrera Targa - 3.2L, Euro pistons, 964 cams, steel slant nose widebody
1975 911S Targa - undergoing a full restoration and engine rebuild
Also In The Garage - '66 912, '69 912, '72 914 Chalon wide body, '73 914
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