From So Oregon you are looking at two very full days of driving to get anywhere I would want to go. So Mag bay is about it by day two. I would love to get just below LaPaz before settling in. I am figuring @ three days of driving. I want to get to LaPaz because that is where the fishing gets really good.
May/June is the best balance of tempratures and fishing in that region. It is warm enough that a beach camp is comfortable. But not so warm that AC is needed for the

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A two week trip can be done if you are willing to do some hard core driving. Obviously with my children that is not an option. If you really drive hard you can make it to Mullaje in two days. That is kind of where I consider the vacation to begin. There are destinations further North that are fun and have great 4x trails to get into. (or at least used to?) But the fishing up North is not as consistant.
One of my absolute rules of driving in Baja is never drive at night South of Ensenada. I have done it twice and hit one cow and very nearly missed another. They come out of the desert at night to lay on the warm pavement. Black cow + black top + a black night = bad juju! In Mexico you are responsible for the cow you kill.
Trip planning is not difficult for a Baja trip. The key is knowing where you are going to fuel up. In dozens of trips down there I have never had any negative encounters with locals or policia. They have always been very kind and quite generous. I love it down there.