I live in San Pedro, and my boat is near your new marina.
I'm tempted to help, but I'm concerned about the little outboard. Do you know how fast it will push your boat? How fast does it burn fuel?
Motoring 50 miles sounds tedious with the outboard and, with prevailing winds, most of your passage will likely be under power. However, winds are coming from all directions these days, and the forecasts are changing hourly. Still, it SHOULD be easily doable in one day.
Do you and your sister get seasick? Do you know?
You'll want to follow these weather sites carefully: