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Regarding going back into drive while still moving at high speed, when i didn't have override control of my transmission i did have some issues if i was traveling at around 60 mph, if i went back into drive without rev matching well the transmission would shift down a gear and rev really high.
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Yes, that is the problem and it can be detrimental.
Automatic transmission design can vary, and whether you can shift back into drive while in motion without incurring damage is questionable. One of the most expensive repairs imaginable on any vehicle is an A/T rebuild - so be careful. Saving a few $$ in fuel is not worth causing well over a thousand $$$ in repair.
I'd suggest you consult with a transmission shop and ask them the question directly. They can give you good reasons why you shouldn't do it, if it can't be done without doing harm.