Jungle seems simple in essence. Gank, and farm on your way to ganking or stop ganks. Get objectives when possible.

But I die when I don't know if I can 1v1 or 2v1 or not. How do I figure this out? Sometimes I'll get a lead then feel like I should keep killing and ganking. But it doesn't go well, sometimes it does.

How can I figure out winnable fights based on items and obviously not memorizing every champion in the game along with their damage output with x item at x level.

I like to play nunu amumu hecarim Dr Mundo. I want to learn to play assassins but I just feed since I always go for bad assassinations. With tanks I'll just cc them and pretty much rely on my ally to secure the kill.

But how can I take my gameplay with both tanks and assassins to the solo carry level?