Size and brightness are only two factors - they are compounded by another key one -- motion. Galaxies, stars and nebula are relatively still from our perspective. Generally, you can repeatedly take pictures of them night after night and, within limits, add up all of the exposures to capture a LOT of light. The Hubble Ultra Deep Field "image", for instance, was the sum of a million seconds of exposures - more than 10 days.
Planets not only circle the sun with a noticeable motion, but they rotate. Taking crisp photos of planets is like getting great shots of fast moving athletes - you'd better have lots of light and a big lens.
Pluto doesn't present a lot of light and it rotates every 6.4 days. That means a feature on the surface will pass across what we can see in 3.2 days. Its position will change by 10% of Plutos visible diameter in just 8 hours. So, to get pictures with a resolution of just 5% of the visible diameter would limit exposure times to 4 hour or less exposures - compared to 10 days for the ultra deep field. Even if Pluto is relatively brighter than the distant galaxies, the task of getting quality photos using even the Hubble become daunting.
The math for this was done quickly, so hopefully, I made no gross errors. Let it be said that even Jupiter, as big and bright as it is, with it's 10 hour rotation it presents a problem for amateur astronomers in getting high resolution. It won't stand still.