>Answer: I have not thought about those two questions, at this point. However, they are valid. I prefer to allow the system to re-name the files to a system generated name. That way each customer will not name the files any name they want which could cause problems later on. Keeping all the format names the same.

You may want to consider implementing a naming convention. If you rely on generated file name, you would need to establish a relationship somewhere in the database to know about that. I usually name those images as per a relational key from a table. So, at least, when looking in Windows Explorer, you can always establish a relation with what this image is related to.