The default maximum file upload size for MOSS is 50MB, with 2GB being the limit imposed by SQL Server. In some cases, like with AutoCAD because of the fact that files are associated with each other, or with large graphic files, I would say stick to a file share, it will be faster and cheaper, but if you do need to store everything in MOSS, here are the settings you need to change:
Changing the maximum file upload size seem simply a matter of changing the following setting in central admin: Central Administration > Application Management > Web Application General Settings

However, this only applied to files uploaded to Libraries, not to attachments to List items, this has to be edited in the web.config

Details of why here:
http://www.synergyonline.com/blog/blog-moss/Lists/Posts/Post.aspx?ID=8
Via STSADM, you can also change the value:
stsadm -o setproperty -propertyname max-file-post-size -propertyvalue 2000 -url http://your_moss_server/
Finally, there is the issue for search crawling larger files, this is adjusted via Central Admin and the registry, (I assume) on the indexing server:
http://admincompanion.mindsharp.com/SharePoint%20Server%202007%20Administrators%20Companion%20Wi/Crawling%20Details.aspx

Then, IIS may need adjustment:

http://support.microsoft.com/default.aspx?scid=kb;EN-US;925083

In the end, I would say test and test again, but this information should help.

Labels: Administration