It still makes no difference. Let's assume 3 images
id o
1 1
2 3
3 2
You retrieve them with "ORDER BY o ASC", which gives you the images with id in this order
1, 3, 2.
If the user deletes image with id 3, you now have
id o
1 1
2 3
And you get your images in order 1, 2 which is still correct.
What you need to do is create logic that deals with the user assigning a new order value to a specific image. But this logic will be the same wether or not you always have a new order value for an image collide with that of another image (like you will if you resequence your ordering to always be one greater than the previous value), or just sometimes (like you will if you do not resequence your order numbers. Only if you never get a collision (which you would not be able to guarantee anyway) could you make your reordering logic simpler.
This is based on my intuition, but it should be possible to prove this using induction.