I think it depends on the crisis of the moment...  Harry has skated on thin ice before for what he perceives as the greater good if he sees no better alternative than to do so.  I am not sure if it is arrogance or naivety on Harry's part when he does this.     

I was thinking that, precisely. Money to help Harry to keep a dignified status. Not money for the sake of it.

   Yeah, from the beginning Harry made it very clear that he wasn't into money or the trappings and comfort money could bring him by choice.  I don't remember the exact quote, but he repeated variations versions of how if he wanted he could use his talent to gain material goods and wealth.  No, he was content and comfortable in his dingy basement apartment decorated in early Salvation Army and Good Will with a book case full of worn paperbacks.   Some of this attitude might change now
that he has a child to support,  but it will be for hercomfort and security, not his own.

    If Jim wasn't just pulling our legs a couple of years ago about writing Murphy's funeral, she could be the one to go.  It would fit the pattern, love Harry and die...

Can't he?  He'd fall, but I think he can.  I think that's why Jim said Lucy wasn't out to destroy reality, and it was more of an argument about being right.

  Didn't say he couldn't, but he won't cross the Boss...  He doesn't want to fall..

The only thing I can add to this conversation is the Dresden Files, and particularly the first three books, are very much influenced by 1940's detective fiction.  In Storm Front, Jim lifted the basic plot structure of "Farewell My Lovely" by Raymond Chandler and made a few clever twists and then added magic.  (Though a very well thought out magic system.)  In both books the detective starts investigating a murder, there is a criminal who is not the murderer but for his own reasons doesn't want the investigator getting involved, there is another murder of someone who knows too much and in both novels it's a women.  I almost forgot the best part; in both books the investigator is involved in a separate investigation, looking for a missing person, but in the end both investigations are really the same investigation.

So all the conventions Jim used to create and animate Harry can't just go away.  They remain integral to who Harry is and how he relates to women in general.  Now if you see the same or very similar descriptions of women in the Alera series or in the newer Cinder Spires book (books whenever we get more), then the criticism leveled against Jim's writing is a much more valid argument. 

Of course, it might be argued that those two series are modeled after genres with a particular take on the world and the people in it.  For example, Jim has said the Cinder Spires is basically Horatio Hornblower sailing ship adventure with a steam punk twist.  I've never read any Horatio Hornblower books so I can't go any further than that.  The beta readers who have read samples of other types of novels Jim has played around with; like a hard scifi X-Files on the moon concept that his beta readers weren't that hot on, might have better insight into this question.     

I have read the Hornblower series but not Cinder Spires...   So I cannot compare...

  The thing is, the story is being told from a male's point of view, i.e. Harry's point of view.  We know from his own description of himself that while he does respect women for things besides their bodies, he is, by his own admission, sexually frustrated.   Not sure if that is the right word for it,  but Harry hasn't had much experience with women..  So even at this point in his forty year life, which includes fathering a child, he physically reacts to the female body like a very young teenager.   In other words it is all about breasts and curves etc., yet Harry also goes out of his way to say how much intelligence in a woman attracts him.... However so far we haven't seen Harry in a relationship with an intelligent woman with average or below average looks.   

I am under the impression that the last Warden of Demonreach was Gatekeeper, and he quit, which is why the island holds a grudge against him.

That has been a theory, but I'm under the impression that Jim knocked it down.... However I could be wrong about that.

Raisins,

If you read the excerpt of the planning between Harry and Kringle you would know Nic's true aim wasn't what Nic would say it was.  Harry and we, at least me, should know this.  Therefore, Nic's primary objective wasn't the Grail but something extra that went unnamed.  And, It likely was the knife.

Now, after you read this above, can you reread what I posted, it might make more sense after being reminded of this conversation and that the Grail wasn't Nic's true aim.

I think his main purpose in getting into Hades vault was to get the Knife.  He must have believed Harry had the remaining object(s) of power on him as he didn't think Anna had them on her.  It is likely he didn't know how many objects there were.  He did know though that Harry had a 'knife' up his sleeve.  (The metal had clinked on something Harry carried and Nic noticed the noise/vibration etc.)

The last time I recall him have a Cup like object resembling the Holy Grail was in Death Masks when Nic and Deidre had Harry imprisoned and Nic decided to bleed him to death.  He didn't have the necessary cup so he had to delay but was interrupted by Shiro before he got it.  So I'm thinking Nic intends to bleed someone then into the cup then use their blood...

I agree with this, but it all backfired when he got what he said he wanted, the Grail..   I repeat that neither Michael nor Uriel were that upset about that fact, which is significant in my opinion..