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I would create a folder in the Images section of the Design Studio specifically for this newsletter, and each week, name the images week1-trending-1, week1-trending-2, etc (or something similar). Each week, you can go into the same folder and upload the images there (and keep track of them all).
If you used the same names, and just overwrote them each week, the files would update in your previous newsletter versions and be lost. If you use the naming convention by week, all you need to do is clone the previous week's newsletter, and go into the HTML editor, do a "Ctrl+F" and replace every week1 with week2. As long as the new images were uploaded and followed the same naming convention.
For deployment, it depends on how much data you want in the program for each send. You could create a bucket program per month, and put each month's newsletters in there. Or you could create a program per week. Cloning will be a huge help here for you!