Best way to securely share file/send link to external client

I'm looking for the best method of securely sharing and/or sending large files (big Keynote documents and videos) to external clients. Basically a YouSendIt-type solution, but hosted and running off of my OS X Server.
What I'd like to be able to do is generate a secure URL for an individual file that can be emailed to a client. I would prefer not to have them need a username/password, but just be able to click and download from the link. I'd also like that link to expire after a certain amount of time. I'm not positive if this is the best method, and am open to other options suggestions.
Would love some advice as I've been Googling for quite a while without any solid suggestions or solutions. Thanks!

Off the top, and I don't know how familiar you are with bash shell or other scripting languages here...
Cleanup is one or two lines of bash in a +periodic daily+ script. Delete stuff older than a week or such via a bash shell find command and an rm, mayhap. That stuff is easy, if it's just a "blindly nuke stuff older than a week" or similar logic required. (Test that rm logic carefully as it really stinks to accidentally rm too much.)
Upload is slightly more involved. Probably a droplet or such, invoking Applescript or a bash shell script to generate a GUID (or a random string) and copy the file into the web files directory. [Here's a start|http://putnamhill.net/codeshop/applescript/applescript_bash.html] toward this; that looks like it'll get you to bash, and you can do what you need from there. Drop a file on the droplet, and you get a GUID-based name generated and an sftp certificate-based transfer up to the server, and a dialog box showing you the filename.
Or you do an upload via a web form that pulls up the file and manipulates it and tosses up a page with the URL for you. That can easily be a cgi page, since this isn't high-volume stuff.
If this stuff doesn't exist, it's a day or two to code it in bash. And perl or php or python or ruby or such could likely be used here, too.
In general: be careful with who and what can be uploaded to your server, too. Allowing a random file upload into the server environment is very close to allowing a server breach. Some of the attacks here are clever, too. (qv: "gifar" files).

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