I had a similar problem with my D-Link 2100 access point and my squeezebox3 (no problems with the squeezebox2). It turned out that the sb3 didn't like the "wireless G with dynamic boost" AND the power output level. Turning off the boost AND setting the power output to a quarter fixed it for me. I saw the same as you, getting a 169.x.x.x address (DHCP server not found) using WPA only, didn't change those settings as I knew they were OK with my sb2. Changed the boost and power level and it immediately got an IP and connected to the silmserver.
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