Spare a Brother a dime

Matthew 5: ⁴² Give to the one who asks you, and do not turn away from the one who wants to borrow from you.

Apparently panhandling has become a profitable business for some in my local neighborhood.  Rumor has it that a persistent panhandler on the corner of Perry and Hwy 98 can pull in several hundred dollars a day.  Scripture is clear here, 2 Thessalonians 3:10 For even when we were with you, we gave you this rule: “The one who is unwilling to work shall not eat.” Yet what do we do when we are confronted personally by someone claiming to be in need?  Often logic kicks in and we feel that we must ascertain their true need.  In some cases, fear takes hold and we feel trapped or perhaps impatience at having our agenda interrupted.  I think often people are professional scammers who know how to leverage our human reaction to make a quick buck.  I confess, that its easier for me to simply cough up a few bucks than to sort through the real need. 
Examining Matthew 5:42, however, gives us no instruction as to the ensuring the need is truly genuine.  This is part of the sermon on the mount wherein Jesus is making a long case about our heart condition regarding so many of societies' laws and rules.  In verses 38-42 we are instructed that we are to be patient, forgiving, and willing to share the blessings we've been afforded.  So to me, every time I'm confronted with someone who states a need, my heart condition is being tested.  Am I holding on to the money in my wallet for my own selfish wants and needs first, or am I willing to let Jesus control my money?  In my view, I must be willing to lay down everything in my life, including my money to Jesus control.  So then why is it so hard to be willing to part with whatever is in my wallet?  Jesus said that whatever we do "for the least of these, we've done for Him."
My belief is that we must be willing to let Jesus be Lord over everything.  If that means we share some of our worldly wealth with someone who needs it, then so be it.  Said another way, I'll quit sharing the $20 in my wallet when I need it more than the person asking.  I'm sure I've been scammed, particularly by one specific individual who frequents our church parking lot.  If in error, I would rather err on the side of giving Jesus control than selfishly guarding the money in my pocket.  At what point do I become the selfish young ruler, unable to give up control of my money?
The Missions Committee at church is trying to address this issue by setting up a small fund with a local person familiar with the homeless issues and people in our community.  My hope is that I can have cards printed with the name and address of an agency that can truly provide real help for those truly in need.  In the meantime, I guess I remain an easy mark.