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Desert Bug is right on with the PIC time needed (1000) to sit in the left seat of most commercial ops out there today. I've had my private for years and recently picked up a bunch more ratings and endorsements. Now just shooting for that magical 1000 hours. A ton of friends have been getting jobs lately, all of them right around 1000 hours.
The FAR's (135) require a minimum of 500 for PIC. You also asked about logging time. To log PIC time, you must be rated and current in the aircraft. In other words, you don't log PIC while TRAINING for your private certificate (except for your solo time). Once you get the ticket, you'll start logging PIC time, even when receiving dual instruction in most cases.
Last, the question on medical. You have to have a 2nd class medical while exercising commercial privileges. In essence, you just have to find an examiner to check you out and certify that you are fit for flight under a 2nd class medical (slightly more stringent requirements than the 3rd class medical required for private pilots).
Good luck!
J
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