I'm one of those people who had a hard time making a confirmed observation of Pluto. I tried with the C8 and then the C14 for 7 seasons at the time when Pluto would be well placed for me. So don't expect it to be easy and don't give up. And it helps if you can arrange for two clear nights in a row.
I was finally successful in 2015. To add to my awe and satisfaction, I saw Pluto just two months after the New Horizons flyby.
Edit: I agree with those who say a good chart is key.
Edited by Special Ed, 10 March 2019 - 01:35 PM.