Pluto is not nearly as difficult as it is often made out to be. The frequent suggestions that it takes enormous aperture or unusually dark sky to see it are probably responsible for most not even attempting to do so. The other obstacle is a good chart that shows the track among stars in the 14 to 15 mag range.
I observed Pluto as a newbie with an 8" SCT decades ago when it was still in the high 13 mag range and didn't consider it difficult at all. It is at least half a magnitude dimmer now, but I have observed it with a 110ED refractor from a dark site in the past 2 years. I have not succeeded with an 80ED so far, but haven't had a night of steady seeing during the attempt. I suspect I could manage it with a 90mm. I have also seen it through the 20" stopped down to 6". My novice son was able to locate it in only a few minutes with his 10" Dob.
The common denominator in all instances has been a good finder chart to sort out the 14th mag field stars. I use S&T's annual chart. I have not had any difficulty identifying the movement across the busy field the next night or subsequent nights. It shouldn't be too difficult with a 14" if you have skies & eyes that let you see stars past about 14.5 mag.
Ceres is a dwarf planet that you can detect at times naked eye.
The other two "certified" dwarf planets I have observed are Haumea and Makemake. These were targets for the 20" in dark sky. I manually plotted their positions on some hand drawn fields based on Wikisky images and MPC ephemerides for each. I was able to observe them over several nights and see their movement against the star field. The only one missing from my dwarf planet set is Eris. It is simply too dim for the 20" by eye.