I've added an Uploader module to Sprint Developers. You should see the link in the menu on the left hand side, but here's the direct link:
http://www.sprintdevelopers.com/modules.php?name=Uploader
It's pretty experimental at this point. I haven't tested it thoroughly but I was able to send a few JPEGs to my phone.
You should be able to use the Uploader to provision MIDlets to your phone. This should solve any caching issues during development. The Uploader is even pretty good at fabricating a JAD file if you don't have one. It extracts the manifest from the JAR and fills in the blanks.
The Uploader will remember phone numbers that you send files to so you don't have to re-enter your number ever time. Eventually, I'd like to add photo re-sizing to optimize pictures for your display. The Uploader will determine your handset model based on the headers it sends.
Please let me know if it works for you (or doesn't) and any additional features you'd like.