Down and out - Blessed are the poor in spirit - really?

I've added the Bible back into my reading. For a long time I've been afraid to read the Bible, afraid to hear the words of condemnation I think it holds for me. So I've started with the words of Jesus, you know "the red letters" in the Bible. Today I read "God blesses those who are poor and realize their need for him". In the version I read there is an * and a note saying it actually just says "God blesses those who are poor in spirit". How far down do you have to go before you'd be willing to beg? Before you give up your last shred of dignity? I sometimes see Westerners in Hong Kong sitting outside a MTR station with a sign saying "Lost my passport and all my money, help!" I wonder "is it a scam?" "Why don't you just go to your consulate and ask for help?" but I don't stop and ask. I don't get involved. Not my neighbor - I guess.. I digress. 

What would it be like for me to be that desperate? Am I there yet? What does it mean to be "poor in spirit"? I hate it when the translators decide to interpret things for me and add "realize their need for him". Shit! If I'm sitting on the side of the road, with a box in front of me, afraid to meet people's eyes - do you think I'm worried about "admitting my need"? My action is admission enough, right? The fricking act of asking for help is admission enough - isn't it? 

I'm not sure where the happiness or blessing comes into this, or WHEN it comes into this humiliation. Some translations say "Happy are the poor in spirit". Does the guy in the picture look happy? I did a google image search for beggar, and except for a few exceptions they all look completely miserable. I have to assume that Jesus knows that - and maybe he knows something that I don't know - misery can lead to blessing. Maybe this is where faith comes in - you have to believe it's going to get better, and commit yourself to honestly facing and learning from this bottom of the well experience, hoping that one day it will get better. 

The promised blessing is "theirs is the kingdom of heaven". I wonder did Jesus' first audience have any idea about what that meant. WTF? What is the kingdom of heaven? I guess one of the benefits of the crash and burn experience is that you are not afraid to ask the questions that pious Christians rarely ask. Rather than ask the questions they parrot the answers they learned in Bible School and Seminary. I know, I did it too. No more.