I have a lot of questions in light of this passage of scripture...
One thing I'd really like to know is whether it's wrong for Christians to request collateral from a borrower? Is that against the spirit of the above passage?
And is it never, under any circumstance, okay for you to ask for something back once you've lent it? Like, what if the person just happened to forget about it and could just use a reminder?
And should we be willing to lend out something precious/irreplaceable in the first place, if we're not even allowed to ask for it back?
If we're not to take Jesus' words here literally (at least not in every case), then to what degree are we to generalize?
I should clarify that I believe we're called to give to anyone in genuine need, who lacks basic necessities—but not necessarily if all they're wanting are conveniences, luxuries, etc. (e.g. spoiling children).
Nevertheless, Jesus never specified how MUCH we're obligated to give to anyone who asks. This is something I'm struggling with, because I'm in a situation where someone in genuine need has continuously come to me for money, and it's getting to the point where I'm wondering where enough is enough—how much am I obligated to give to a single person? This person is a family member, and is constantly borrowing more money, and doesn't seem to have any plans of repaying his debts to me. But according to Jesus, I'm not to ask for—let alone hope to receive—my money back, right? But at what point can I stop lending to this person further? once I find myself penniless??? What do I do?
Sorry to throw so many questions out all at once, but it's driving me crazy, and I'm going to have to deal with this person again very soon. I overheard him discussing his need with someone else, saying that he was probably going to have to ask me for the money. He's in need of $200+ because of some overdraft fees from checks he bounced, but I've already lent him $180 for a water bill he forgot about & $250 for his medication just this month. At this point I'm feeling rather put upon, and I'm really starting to smart for it. I don't have a lot of peace about the idea of giving him more at this time.
But Psalm 37:21 says, "The wicked borrows and does not repay, yet the righteous shows mercy and gives." And Jesus does seem to imply that we're to give, even to sinners, and those who do not repay, because we're to be merciful as our Father is merciful, who is kind even to the unthankful and evil. But...to what extent?

Any sound, godly advice on any of my questions would be much appreciated.
I've only within the last 8 months acquired my first job, and am by no means rich. But I am God's steward, and I count what I have as his. I am purposed to do what he wants me to with any riches he entrusts me with, and won't set my heart upon them. More than anything, I just want to be in line with his will. But...where do I draw the line with this beggar?
Also, feel free to discuss anything related to the topic in this thread.