Kathy, Rachel, Dena and no_one,
Thanks for your insights. I have to admit, the timeline I lined out is aggressive and wouldn't leave much room for unforeseen events.
What triggered this idea was the realization that in all likelihood we have to relocate for a new job and both my wife and I would have to build a new set of friends in the new location. Since one of my wife's concern about me being more open and presenting as a woman is a feeling of embarrassment in front of her friends, such a move to a new location would eliminate that feeling.
Clearly, there are softer approaches as well, such as trying to find a job as a male in January in a trans friendly workplace, relocate and go full time except on the job, but build a new net of friends who only know me as trans and then transition later on the job. And, save the severance pay for transition related expenses. However, even that scenario would be tough for my wife, since she would lose her husband for good if I presented female at home 24*7.
Again, thanks for your input, sometimes it is good to have friends who hold you back a bit before doing something that can backfire. It is just that the emotional appeal of speeding things up and grabbing this opportunity now is really huge!
HM