Yes, S/R will only send the entire file once and then from then on will only send any changes. For binary files like images, any change will resend the entire file. Any changes to text files will only send the smallest amount of data needed to describe the changes.
Yes, this would be a good time to do these types of things. Note that the data will still need to be S/R’d to the internet at some point, but it should only be a one-time thing.
The biggest issue to adding large images is for anyone who gets the project later (like a year from now) and they now need to download all the large images for the first time. Obviously, if this is done via a non-internet S/R too, then it won’t be that big of a deal.