I recommend that you update your OS to 10.3.9 to get all the fixes Apple released (including security fixes). You can do that with system update in the control panels
also it's a bad idea to call a folder ".programs". Starting a file/folder name with "." have a special meaning, which is "hide this from finder". You should not be able to see that unless you hacked your system
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Attempt to release a printing object without first doing a retain!!!
2005-05-17 10:37:37.873 Safari[391] Error restoring window from dock: -4960
I don't know about this output, but it's not generated by OpenTTD. Hopefully I will find a way to get it to print whatever OTTD says and only OTTD in one window.
as for the problem: you should not have this problem when you put .app and data next to each other.
I have two things that you could try:
1: try 0.4.0 if you are using a different version
2: put the TTD grf files+sample.cat into OpenTTD.app/contents/data/
2 should not be needed, but if it fixes your weird problem....