Re: the timing of your planned run and assuming you can't buy a copy, see if you can borrow a copy of Jimmy Cornell's World Cruising Routes
from another yachtie; it's as good a distilled description of weather and cruising routes as anything in print. His routing advice & recommended waypoints fold in consideration of prevailing currents as well as the shift in the monsoon season up your way. My own hunch is that you might be leaving a bit early.
Re: arrangements with delivery crew, it varies widely and will depend on how popular your destination is and how eager the crew to have an experience vs. viewing their presence as meeting your needs. A friend has just finished an Atlantic Circle plus a year in the Med and, on every leg, had crew willing to fly out to join him, fly themselves home, and his obligations were only to look after the boat's expenses; they all shared in food costs. OTOH he was moving between popular cruising venues and he was always near a large supply of interested sailors - the UK, N Europe and N America.
Along with the web & the yachtie grapevine, you might consider using http://www.crewfinders.com/index.html
- my friend had some good crew members come from that source.
Good luck on the passage!