I think I can answer a few of those questions:
Back to the childhood home for practical and thematic reasons. Practically-speaking, it's ground that Bond is familiar with and where he is comfortable. All throughout the film, he has fought Silva on Silva's terms. For the psychological boost, the "home turf advantage" element, he chose the Skyfall estate. It also would throw Silva off, who has bested Bond in tech, in London - all over, in fact - so now Bond is in an old mansion? Couldn't be easier, right? The guard is down.
Thematically, he goes home because Bond and M are confronting the past and trying to escape their past demons to move forward. It also brings out that theme of "Old v. New" that plays out the whole movie. The question since reel-one of Skyfall (in the viewers' heads) is, "Is Bond too old? Shouldn't he just leave everything to the younger, hipper spies like Q?" We see him physically fail, we see him bested by tech and Silva...can he get out of that rut and prove that experience, wisdom, and being old is not the detriment others think it is? Plus, we want to see him escape his past demons haunting him.
They left quickly, so maybe they didn't have time to stockpile weapons. They probably should have grabbed a couple carbines, though. Still, for the nasty, dirty, up-close fighting they planned, booby traps and shotguns were fine.
I was kinda glad it was Finney. Connery would have made it weird. It would have been like Lazenby breaking the fourth wall.
M being awesome? Don't mind it.
Bond being macho? Don't mind it.
Bond crying? Don't mind it. (Also, can he be too macho, yet also cry?) This doesn't ruin the character for me. He's always been a human who can bleed, cry, and die. He just doesn't let most people see him do any of those things. (Never let them see you bleed...one of the all-time great Q moments...)
Knife to a helicopter fight works in an action movie. Don't mind it.
I'm not sure what you mean by "going all Joker"...?
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