What would be the easiest way of quickly mailing a file through GMail?

"Doing for Gmail what the MailTo link does for Outlook, the wonderfully simple gAttach is a small utility that reassigns Gmail as the default mail account from Windows documents. With gAttach installed, selecting Send from Windows Explorer, Firefox, and Microsoft Office automatically attaches the files to a Gmail composition.

gAttach is freeware."

"I have upvoted the Dropbox and Google Wave answers, but perhaps the dragdropupload addon for Firefox would suit you? Not quite automated, but will save a bunch of time. Simply drag the file(s) into the gmail message instead of selecting ""attach a file"" and routing through folders.

Drop files into attachment boxes instead of browse for them or type in the filename. Drop multiple files"

"It may be worth it for you to check out Drop.io - While it doesn't have a lot of FREE file space, it still has some and it does realtime collaboration. It's very groovy if you ask me.

100 mb limit, so great for small file transfers, and has hidden url or public url and other features. For $20 a month you can get the HUGE storage version. I'm not really into paying for software though unless there is no free alternative. However drop.io does let you create as many free accounts as you want, infact they encourage it.

It's very cool technology and pretty tough to explain, check out the vid in the link."

Use a mail client like Thunderbird 3. Since installing is a problem, you can also use Portable Thunderbird. Configure Thunderbird to use GMail. Then goto the folder, select all and click on send to -> Email client. The pics will be sent to Thunderbird 3, provided its the default client and you can send the mails.