A Gospel Picture (And a plea for wisdom)

I really like gospel pictures:  life stories that demonstrate the gospel message of Jesus without actually telling it.  A few weeks ago, I saw Frank again, and a gospel picture happened.  Frank, if you haven't read before, is a homeless guy whom I'd like to someday call my friend (a term I'm not wishing to use lightly here).  I have a vision for Frank:  plenty of us have given cash or a banana or a gift card to the homeless cardboard-clutching beggar on the corner before, but who has ever gotten to know that beggar, simply befriending him and earning his trust to show him he's a valuable human being created in the dignity and likeness of God?  I know I never have, but God keeps placing Frank in front of me and I feel this is God's vision, or at least part of it (Ephesians 3:20).

Seeing Frank at the usual spot on my lunch break one day, I parked my truck and walked over with a full lunch hour available to him and offered to take him to Burger King.  I didn't want to give him a hot meal as much as I wanted an excuse to sit down and talk with him.  He refused, because he had already had been given a lunch he said, but he said he'd take me up on the offer next time.  I left him with prayer and some food.  I prayed that he would see God's Fatherly love in His provision of basic needs for Frank, to which Frank enthusiastically responded, "Amen! God bless you!" 

That was encouraging.

But as I walked away, I was encouraged even more in thinking about what food I'd left for him:  some leftover La Cocina tortilla chips & salsa, given to me by my parents when they took me out to eat two days before; and a pumpkin cupcake, one of many given to us by Cristina's friend Jessie they day before.  The Spirit  whispered:  "Freely you have received; freely give" (Matthew 10:8).

The peanut butter & jelly sandwich from our own kitchen, I had already eaten for myself.  But the gifts that had been given to me, I had just given away.  And I thought....what do I own that has not been given to me by God?  How generous has God been to me in giving the saving love of Christ that I don't deserve?  And yet, how stingily have I been clutching on to the things that are "mine"?

And I saw a gospel picture:  Jesus was essentially telling his disciples in Matthew 10, "I have loved you so abundantly and set you free from your chains.  Go and do likewise, setting others free from their chains."  He commanded them to heal the sick, raise the dead, cleanse the leprous, and drive out demons--just had He had healed their sickness, raised them to new life, cleansed their leprosy, and driven away their torturous demons.

******

I saw Frank again today, again with a full lunch hour to spare, and things didn't go as expected.  I thought he'd take me up on my offer as he had said he would, but he seemed anxious to sit on the corner in hopes of another $15, seeking to keep his remaining possessions from being auctioned away by the storage facility he's renting from.  I'm thinking of helping, but I've heard a lot recently about how our "helping" can actually hurt someone. 

But when does helping hurt?  Any ideas?  I know that I can't simply do life for Frank, that there's some things he needs to work through on his own, but is this one of them?  Could this be a doorway for further gospel conversation, a step towards authentic relationship that honors & emulates Christ?  Or is this a step away from that, a hindrance?  I'd appreciate your humble wisdom in comments.  Thanks.