Hi April,
Importing the data first without the image/uploads is fine. The next step would be to create a CSV of recordnums, the fieldname the files are being uploaded to, the tablename and the image filenames:
recordnum,table,field,image
1,records,uploads,image001.jpg
1,records,uploads,image002.jpg
1,records,uploads,image003.jpg
2,records,uploads,image004.jpg
2,records,uploads,image005.jpg
3,records,uploads,image006.jpg
4,records,uploads,image007.jpg
In the above we're adding the images to the field 'uploads' in the table 'records'. This assumes all the images are in the same directory.
Creating the script is something that would take a bit more time and space than we have available in the forum - if you aren't comfortable trying it yourself we could look at building one for you but that would be more of a consulting request than a help request.
If you'd like to ask for a quote, you can email consulting@interactivetools.com with the details (just include a link to this thread).
Of course, if someone has already written a function to do this then let us know!
Let me know if this helps,
Tom