Mains in sub optimal position vs less experienced champion

So I would love the communities thoughts on this. I am an illaoi main (mastery 6 just waiting on essense for 7) I have dabbled with various builds and have a lot of playtime on her. Recently with my premade I moved from top lane to jungle and have tried various picks of the usual variety (skarner, rengar, kha'zix, zac etc) but the last couple of times I decided to pull out illaoi jungle for a couple of matches and it worked solidly with the patch 6.11 changes. My clear was faster and safer then on some of the junglers i had played previously although it relied on a short setup like maokai and shaco. First match I got very fed with an S rank and the next two I was able to make solid impacts. Bot lane ganks were flat out broken post 6 due to soul grab + ult with a cc heavy support. So my question is: Is a champion you are very experienced with a better or simply viable choice as opposed to a champion whom with you less experienced but is more high tier pick for the role? Obviously this is for characters who can actually perform a role without being completely screwed over.
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