Originally Posted by
aHappyCamper
Am I insane for even letting bicycle transportation from San Diego to Arizona even cross my mind?
No, and it is a beautiful ride.
However, I would probably work yourself up to it a bit so you have confidence of getting up and over the mountains and be able to cross the gaps in-between. For example, work first to get yourself to ride a weekend ride to a place like Julian (4000ft). One day up and the next day back down. That will give you a reasonable feel for the other parts overall.
It is possible to do this ride without carrying camping gear but you'll need to be able to cover some gaps (e.g. San Diego, Julian, Brawley, Ehrenberg, Aguila, Tempe is what I rode - there are some more places to stay in-between but not many). Alternately if you are camping, you'll have more flexibility to break it into more variable pieces and adjust if you can't make the full distance for some reason.
As you know, you'll occasionally get snow at higher elevations above San Diego in Christmas time. I've ridden through the mountains above San Diego a few times and had some weather: March 2001 (snow in Julian), December 2002 (fine), December 2003 (snow), December 2006 (rain & sleet).