I can't imagine needing anywhere close to that amount of stuff. Trim it down - way down. You're not going to the middle of nowhere, you can do laundry, pick up anything you need if you run out - they have the same Wal-mart, etc. in San Francisco as they do in NY.

Keep in mind, if you're counting on falling back on gate-checking the carry-on(s) if there isn't room in the overheads, that means you won't want to have anything in the carry-on of value (cameras, electronics, cash, medication, etc). But I'd avoid that much luggage and carry-ons to begin with.

Oh and be sure you include everything in the measurements for the carry on size limits - handles, wheels, anything sticking out from the main body of the case.