Parking is easy, as long the gate is open. Cops used to come around and didn't really like when people parked in the cul-de-sac. A lot of guys leave their cars parked there anyway. I always just unload there and then park in one of the many diagonal spots along the 87th street. You will have to launch from Calumet park if the gate is closed.
If you follow the path from the cul-de-sac straight to the lake, you'll get to the place where most people get out of the water. It's behind a guardrail and no trespassing sign (I think that's what it says
Upwind from there, maybe 40ft away, is concrete slab where most guys launch from. Launching is very easy. If there's a wind by the shore, you can just set your board on the water, step on and sail away. In case of no wind by the shore, you'll have to throw your board and sail in the water, swim 20-30 ft and water start.
Getting out of the water is trickier. I bet that's when Ady damaged his equipment. I always:
1. detach the sail from the board (the water is about waist deep)
2. set the board on the concrete, the tail of the board and fin over the concrete edge
3. lift the sail out of the water and set it on the concrete
4. climb up the concrete and carry the board and sail up over the guardrail separately (remember it's not the same spot you launched from)
All of this is a lot easier if you talk to the guys before hand and agree to get out of the water at the same time. That way, one can climb up the concrete and the others will hand him all the boards and sails one by one.
Hope that helps.