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Thanks for the reply. It will be a very hands on job, lot of images to be replaced but if that's what needs done then that's what I'll do. No point in skimping on the work during a content improvement campaign, right haha To be honest I almost knew already that I'd need to 301 them all - I just wanted there to be another solution, maybe I'll be lucky and find a nice easy rewrite match. Good to get a second option on this tho. I'm going to hold off marking it as answered for a little while and see if I can get some more input while I prep the job.

Thanks, Moosa. The "What Should Be Accessible To Users & Search Engines" section answered the majority of my question but I'm going to hold off just a little bit longer and see if I can get a few more answers or reading suggestions on the wordpress dupe issue. Thanks again!