To anybody else struggling with this, I found the solution for my problem. Not even support could figure this one out unfortunately.
It seems that shopify will through these errors for numerous causing factors, as you can see on this page people were able to resolve their problems with other solutions.
Mine was the Image Position column being blank, I had configured everything on the CSV file spotlessly with the exception of leaving this column blank so I was getting these errors accusing something else being the problem where in fact there was no problem there. So there it is, make sure the Image Position column is filled out if you're adding multiple images.
|Handle||Title||Body (HTML)||Vendor||Type||Tags||Published||Option1 Name||Option1 Value||Option2 Name||Option2 Value||Option3 Name||Option3 Value||Variant SKU||Variant Grams||Variant Inventory Tracker||Variant Inventory Qty||Variant Inventory Policy||Variant Fulfillment Service||Variant Price||Variant Compare At Price||Variant Requires Shipping||Variant Taxable||Variant Barcode||Image Src||Image Position||Image Alt Text||Gift Card||SEO Title||SEO Description||Google Shopping / Google Product Category||Google Shopping / Gender||Google Shopping / Age Group||Google Shopping / MPN||Google Shopping / AdWords Grouping||Google Shopping / AdWords Labels||Google Shopping / Condition||Google Shopping / Custom Product||Google Shopping / Custom Label 0||Google Shopping / Custom Label 1||Google Shopping / Custom Label 2||Google Shopping / Custom Label 3||Google Shopping / Custom Label 4||Variant Image||Variant Weight Unit||Variant Tax Code||Cost per item|