My player character is usually necro or cleric (although I have started games with vampire and dragon), and I then hire the rest of the available set on the Dagger Wound Islands. That leaves me with either 2 necros or 2 priests. I swap Simon Templar for Ithilgore as soon as I get to Ravenshore (you can avoid the dire wolves completely by walking west along the shore). I save up my horseshoes to get Ithilgore to Master asap (gives him Flight) and I swap the spare necro or priest for Cauri as soon as I get the necessary scrolls and find her.

I tried one game where the objective was to hire all the high-level help as early as I could, but it was boring. You miss out on virtually all the character development for your party, and the fighting is way 'way too easy.