Pro’s: Can bring minor speed and security improvements; more noticeable on larger, heavier or more complex websites and webapps.
Con’s: Adds another layer of complexity to your hosting / publishing configuration. Aggressive caching can become irritating.
My personal opinion is to only use services like Cloudinary / Cloudflare if you have the expertise to diagnose and troubleshoot any problems that may arise through their use. For the average RapidWeaver user, there probably isn’t a hugely compelling reason to use them.
I do not include anything in my image stacks that would prevent their use with these cloud services. But ultimately it’s not really something I can test for and kind-of outside of my support remit.