Hi stoneydork, welcome to Orchid Board!
I can see how what you're reading would be confusing. Here's the deal: if the plant's roots are healthy and it's not in danger of rotting in the old medium, you can wait to repot until the blooms have dropped. If the plant's roots are not doing well and the medium is nasty, it's better to go ahead with the repot and potentially sacrifice the current blooms for the sake of the plant's health. (The blooms won't always whither due to repotting, but you always run that risk.)
Your roots look nice and healthy, so I'd just leave them be and enjoy the flowers.
As for your choice of future pots, I wouldn't go up in pot size by too much- orchids like to be on the snug side in their pots. I love using clear pots for my orchids because I can see their roots and use that as a guide for when to water them. Perhaps you could repot in an appropriately sized clear pot, and then place that inside your larger decorative pot. But that's just what I would do, and there are many ways to go about growing orchids. Good luck with your beautiful new plant!