"Should DWCC have picked up on that? In other words, will I have to hand code that every time I make a connection to database?"
No, DW does not have a way of setting the character set.
like i stated in my previous reply, if you use the webAssist Dynamic Connections behavior to create the database connection, you can set the character set, if you use the DWE connection, you will need too manually change the character set.
as for the image name, you are using the standard DW update record behavior. this behavior is limited in that it can only use form information.
for image upload, you need to use the Data Assist upload record behavior, and bind the image columns to the WA Uploaded Files(File field name) -> Server file name variable that is created by the upload behaviors.
please revisit the tutorials for adding file upload