First off.. your questions are very legit, and not stupid or newbie like at all. So far you have good questions..

As for the upload script.. I plan to create one for almost the same reasons and I am sure that it can easily be modified to fit your needs once I get it done. I am working on some other stuff first, but probably this weekend my to do list will be down to that level

especially if it is going to rain in this area and I can't be golfing, or softball or anything

Just keep in touch either through pm or email (bradc@addictedusers.com) and I will see what I can do to help you with this.

Unless others want too. (that are far more superior in php than me.. lol)