Contradictory Finances

 I am trying to process what, to me, is an obvious contradiction so close in Torah:  

Devarim 14:4: Forgive a loan easily in the shemitah year, but, in reality, if you follow G-d's Word, no one will need to forgive any loans since "there will not be among you anyone destitute" if you follow the Word.  

Compare:

Devarim 14:15: You shouldn't think twice about giving money to charity - and not harden your heart and "feel bad in your heart when you give" especially because "there will not cease to exist destitute people within the Land."  

The only difference is the conditional nature of the two laws: forgive a loan, but you won't have to, since there won't be anyone destitute if you follow the Word; you'll always have the opportunity to give, because there will always be poor people.

This can lead to what seems like an extremely frightening conclusion: if you abide, then there won't be any poor people, (but people won't listen) so there will always be poor people.  But even then - they, too, are entitled to charity, and always will be.

The reason I say scary is because - yet again - our Torah leads us into territory which makes us extremely uncomfortable - is it possible, then, that economic poverty has something to do with not hearing G-d's Voice and attuning our life as such?  And is there something to what I always perceived to be a twisted misunderstanding of G-d wanting us to be "rich"?

I mean, look at what the Torah so very clearly says - if you observe the mitzvot - because G-d will bless us in the Land, "but only if you will listen carefully to the voice of H' your G-d to observe, to perform, in its entirely, this commandment that I command you today..." - then no one will be "destitute."  

And does this fit in (and when I ask the question, it's already redundant) with the mandatory tithes to the Levi'im, and the orphan and window and ger (stranger?) - will they one day not need charity or loans?

It's a lot to process, which is unusual since the text is both so clear and so contradictory.  More to follow...

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