Well, afaik, this is not possible using regular html/php. I have been working on something simular the last couple of weeks, and all I lack atm is support for multiple uploads :/
However, if it is acceptable to write a client side application to perform the task, this can be done in a number of ways, neither of them having to involve a direct connection to your database.
I assume the server you're uploading to runs on a linux/unix system (if you're using wintendo, may God be with you).
It seems like the people who are going to upload pictures is a more or less controlled group of people, since a client-side application is acceptable. My primary suggestion would be to have the users attach all the pictures to an e-mail, and send them to some specific address. That address would use procmail and a set of (perl)scripts to process the incoming data. You'd probably need to invent some sort of authentication system to avoid other people from "spamming" your database.. Or you can put them in a "queue" table for later verification.
Another solution, like you mentioned, would be to write a simple application (in delphi, C, VB or whatever) that uploads the images to your server.. This can be done in several ways, but the preferred would at least use standard protocols like http, ftp, sftp, scp or similar. You could write an application that performs a post method upload to a php-script if that is preferrable (and all it has to do is to repeat the operation with different filenames). Or you can directly scp them to the server, and crontab a script that checks for new images and inserts info in your database.. Or simply have the user upload them by FTP and use a similar crontab script..
Plug-ins for NS/IE is another solution, though I have no idea how this would be done.
Hmm, its almost 2:30 in the morning, I'm too tired to think! ;> still hope I was some kind of help.
