My wife has offered to drive a sag wagon with the kids if I wait 5 years to do it. At that point she wont be working. We may have another kid and that would put her being about 1 month along were I to start the ride next June. That may not be so great for our relationship. 5 years from now (25th anniversary of being cancer free) my daughter would be 11 and able to do some days with me.
My wife did agree to drive sag wagon for other long rides next summer though so I can at least do a ride from Frederick, MD to Chapel Hill, NC and possibly down to our family farm in GA. I suppose if I have 5 years to plan my XC trip and do other 300-600 mile trips until then I'll know what I need by the time that I go. I should have plenty of time to figure out which route has the most 3g/4g cell coverage. :-P
As for funding...
I wouldn't mind doing it with a charity as I've done fundraising for charities before; however, I don't think that Team in Training does any events that go across the country. The trouble I foresee with doing it as a charity thing is that people may have different opinions about what charity to do and I'm way picky about how much charities receive from donations after expenses. TNT gives 90%+ to LLS (iirc) but some others are much less. Unfortunately, too many charities pay their executives far too much and this dilutes the amount that is given to the causes they're supposed to support.
To be honest, I'm planning on paying for it on my own except for what I can get for free. If I were to start a charity for it then it would be mostly to try to get food donations. I wouldn't mind monetary donations but I have an issue using them to support myself (or my eating) unless it's part of an organized thing and it's planned ahead of time so I'm able to tell people details about where the money would go or at least what percentage would go towards the chosen charity.
As for the route...
I grew up in Tacoma, WA and lived for about 8 years in Santa Cruz, CA so I do know that y'all are right about the winds. Given that, I'm thinking that what I'll do is go from Baltimore, MD to Anacortes, WA for the wheel dip, catch a ferry to friday harbor for an overnighter, then catch another to port angeles and ride around the olympic peninsula down to Hoquiam, WA where I have some family then go back to Tacoma/Seattle for the STP.
The other option would be to RV it to WA, go to the San Juan islands (I love Friday Harbor if you can't tell) then ride back to Seattle to do the STP and continue going south to SoCal and then go east.
Thanks for the tips everyone!