Emailer v2.o (September 16, 2009)
This is a little Windows program that shrinks pictures down to emailable size and then emails them. Uses its own email server so no need to configure anything, works right out of the proverbial box.
Note that to keep things simple there's no installer, just download it and run.
Using is pretty straight-forward: fill in the addresses you want to send to (separate multiple emails with a comma) and drag pictures onto the large text field.
v2.0 (9/16/2009): changed the SMTP port to 587 so it should work even with ISPs that like to block ports. If you have no idea what I just said, don't worry about it.