I fall in to the "have fun" crowd. You should enjoy your dressing and your plan makes it sound like work.
I also question your statement that you are a "Cross Dresser". Are you sure you aren't angling for transitioning to being a woman full time? You're plan are very detailed with regard to changing your appearance to be completely passable. Are you going to try and keep your male and females selves separate? Just some questions I think you need to answer for yourself.
