you really have several issues you are dealing with
1) database
if i were you, i would think about using a table like this:
IMAGES
id - integer
user_id - integer, refers to the id field of the user table
filename - an image's filename like 'foo.gif'
is_default - either 0 or 1, depending on whether the image is default or not
if a user has 3 images, they would have 3 records in that table. one of them would have a '1' in the is_default field, the other two would have '0' there.
2) storing images
There are a number of considerations here
what if you get a bazillion images in a single directory? you might have performance problems
what if the user uploads two different images with the same exact filename? you might overwrite the first image. do you rename each image when they upload it? do you warn them if they upload two different images with the same name?
3) managing images.
If a user wants to 'replace' an image, you would have to choose which one to replace or let them do so. this means you need to design your form to display the correct info to the user. if i were you, i would not permit any user to upload another image who already has 3. i would make a form that shows their existing images with a 'delete' button next to each one. hitting 'delete' would submit to another form which would remove the image from your server and delete the corresponding record in the db.