(1) Doing the LL.M will not help me find a job in the U.S since there are no positions for LL.M's this year and probably for some time..... (recession and in general)

(2) Doing the LL.M will not help me get a job back in my home country, as it makes no difference, not even in the salary level, and the experience (time lost) will be more important.

(3) Doing the LL.M will cost me a fortune and my life's savings.

(4) I'm not particularly interested in academic career because I'm more interested in 'money'...

(5) Living expenses in U.S will be much higher than in my home country...

(6) Doing the LL.M will not even help me qualify for the NY Bar Exam, which I can do without the LL.M (and which won't be of any use to me regardless).

Why do I want to do an LL.M ?

Assuming each of your points are true, then I think the answer to your final question is "you don't". As for your question posed in the title to the thread, you may want to consult a trained professional; insanity is often quite relative on an internet forum.

It might also be worth identifying a range of jobs in which you actually are interested, and seeing if an LL.M is something those employers appreciate. While a given firm may not care if you have an LL.M, there may be a more specialized position elsewhere which would be much more enthusiastic about an applicant with a graduate specialization. (Perhaps a tax boutique, for example?)

Do not fool yourselves... the LL.M. job market in the US is now officially dead (and will remain dead for a while)...

Do not fool yourselves... the LL.M. job market in the US is now officially dead (and will remain dead for a while)...

Do not fool yourselves... the LL.M. job market in the US is now officially dead (and will remain dead for a while)...

Disagree yet again

It is not as big or alive as it has been in the past but it is far, far from dead

Job market's always been dead for under-qualified candidates shooting for top jobs

didn't mean any hostility by the way, realised it sounded quite wrong the way it came out. i meant one should start lower and work one's way up when it comes to job apps

Agree with the fact that the US markets are slow but other than that a lot depends on the markets in your own country? I see most countries (esp. asian) as being more employee friendly than ever before. I am from India and have never seen a boom as this in the job market - the starting salaries here and hitting the roof!
Also, if you have the right work-ex and you do the "correct" LLM (and please dont disregard the bar!), you have a fair chance. Not necessarily US, but please consider the markets elsewhere. Time we move beyond!