Magento Shop - 350 Product addition

We have about 350 product images -- I have attached a few for examples. 1. The canvas size of each image needs to be square (not rectangular) -- many of them already are square, but we need to make sure they are all the same. 2. They need to be placed in the #2 spot (not the main image) for each product All images are categorized by Brand and image file names include product model number which matches the product title. If you can do this, please give us an estimate on time and cost.