Adam,

It's really so simple that once you do it a few times you'll wonder what the difficulty was.

The size problem is also quite simple.  You need a "picture resizer"

Seriously.

What these do is take your image file and reduce it to a smaller size.  How?  I don't have a clue.  I just know they work.  It makes them upload and download quicker and takes less space on the server.

If you do a search for picture resizer you'll get a few jillion hits.  If you are using Xp I like Microsoft's Power Toy resizer (see http://www.microsoft.com/windowsxp/downloads/powertoys/xppowertoys.mspx)

Someone has a version for Vista, but I know nothing beyond what it says on the site (http://imageresizer.codeplex.com/)

There are lots of them out there.  If you try one and don't like it you aren't married to it.  Try another