Just an update on this, I'm not sure what the issue is. I was finally able to re-write timthumb and get some logging because my host basically refuses to get me the php logs. Here is what I'm getting in logging...
TimThumb Debug line 1085 [0.096342 : 0.007037]: Is a request for an internal file: /PleasantView/wp-content/uploads/2011/08/clip_image0023.jpg
TimThumb Debug line 1085 [0.094562 : 0.007359]: Is a request for an internal file: /PleasantView/wp-content/uploads/2011/08/39w.jpg
TimThumb Debug line 1085 [0.112154 : 0.015799]: Found file as //boswinfs02/home/users/web/b2048/ez.001pv003/PleasantView/wp-content/uploads/2011/08/clip_image0023.jpg
TimThumb Debug line 1085 [0.111465 : 0.016900]: Found file as //boswinfs02/home/users/web/b2048/ez.001pv003/PleasantView/wp-content/uploads/2011/08/39w.jpg
TimThumb Debug line 1085 [0.133363 : 0.021210]: Security block: The file specified occurs outside the document root.
TimThumb Debug line 1085 [0.134354 : 0.022889]: Security block: The file specified occurs outside the document root.
TimThumb Debug line 1085 [2.392520 : 2.259156]: Trying file as: //boswinfs02/home/users/web/b2048/ez.001pv003\\boswinfs02\home\users\web\b2048\ez.001pv003\PleasantView\wp-content\themes\newspress\thumb.php/PleasantView/wp-content/uploads/2011/08/clip_image0023.jpg
TimThumb Debug line 1085 [2.418915 : 0.026383]: Could not find the local image:
TimThumb Debug line 1085 [2.423611 : 0.009982]: Adding error message: Could not find the internal image you specified.
What I don't understand is the path "//boswinfs02/home/users/web/b2048/ez.001pv003/PleasantView/wp-content/uploads/2011/08/39w.jpg" should be right...
CAN ANYONE HELP?