If switching boots, I'd recommend either Ninja Tabi or Zerker Greaves based on the other team or how you want to play, Madred's Bloodrazor/Wit's End are also good alternatives.

I would start with wraiths, head to red, then wolves, back to wraiths, and then blue. Leashing/help is very useful and gank/buy when necessary.

Pros: -Very strong late game
-Can destroy a squishy roaming
-Good heal whilst jungling
-Ult/slow can help chase/escape
-Life steal with his 'q' is a good combo

Cons: -Not to great early game
-Focused if not built tanky
-CC shuts him down