My clients/family/friends/members/etc are relatively computer illiterate. Frequently they upload
images that are wayyyyyyyyy to big. This results in a long wait time only to result in an error
message. Is there an easy fix for this problem?

This involves precisely the type of thinking upon which this site is based.

There is a freeware program called Shrink Pic.

Easy to install, small, unobtrusive, fast and quite effective. This program has the capability of
resizing images (gif, jpg, png, bmp) AND convertinmg them to jpg. This all can occur AUTOMATICALLY
just prior to the image being uploaded via your upload form.

Please do not take the position 'My clients don't want extra software on their systems' - any
businessman worth his salary WANTS every tool at his disposal that make things easier,
faster, more efficient and less expensive. Especially when that tool is FREE.

How it works

Shrink Pic runs in the background. It has a taskbar icon which tells you it's waiting for photos to be sent. Then, when it detects that you're sending a large photo, it automatically creates a temporary copy, resizes it and sends it instead. It gives you a notice message, so you'll know the photo you sent was resized.

Of course, the original photo doesn't change, only the temporary copy. You can control how Shrink Pic resizes your photos. Select between three automatic resize levels or enter your own custom sizes.

Shrink Pic also recognizes rotated photos (portrait layout) and resizes them intelligently, so you don't need to worry about that too.

I use it for my family's website. All of our relatives nationwide have it installed on their computers.

Once the image is uploaded, I create a thumbnail using my own php resize function (see Server-Side Image Resize).