Suitability of the stock cooler depends in part on loading. Long periods at near full load may result in higher than desired noise and temperature levels. It wouldn't hurt to start with the stock cooler and add a third party cpu cooler if it proved necessary. In a good case upgrading a cpu cooler should not be difficult.
Quite true, 32GB would be much better.
Depends on what is more important. Editing 4K content would be better done with a 4K monitor with color fidelity. OTH if gaming is more important, then a higher refresh rate might be preferable. As to size, 32"+ would be better for 4K, but 27" is pretty good. It comes down to personal preference so I'd suggest visiting a store and checking out options.