The topic may have exhausted itself as people are now talking in circles.. everything said of cause make sense
- plan what you want to do and then do your plan (tax, legal, etc). which OP already seem to be on the top of.
- don't come here (or in fact anywhere) complaining how hard it is to cut it (or would be to cut it) on miserly 250-400k a year especially without the requirement of working to death. you get face punched and extremely well deserved one. just don't do it as it speaks of you as arrogant and ignorant.
- don't come and state Manhattan is the only place that is livable (variant walkable, has good schools ,etc). again ignorant and arrogant , and not specific to Manhattan (could just as much be replaced by Gold Coast of Chicago, Winnetka ,etc.). saying 'I want it' is ok as that is opinion vs claiming something as fact.
- if you want help/advice, open your eyes a little and hear others. if you are not willing to hear, why are you even here? step out of your shell
and most important, do what is right for YOU ! I don't want to be morbid but your time (and health) is not guaranteed and never was. be it time for yourself, time to give something back to the world (which rewarded you greatly), time to spend with those you love especially your kid(s), that is time you will NEVER get back. Shareholders, investors, blah-blah-blah, all of that is noise that would forget you the moment you are no longer useful to them. live your life, that is the point of this site. try to live every day as your first, your last, and your only one...