I only read through the first 4 pages of this, but here's my 2 bits.
Mathew 7:6
"Do not give dogs what is sacred; do not throw your pearls to pigs. If you do, they may trample them under their feet, and then turn and tear you to pieces"
This woman would be both a dog and a swine, and it sounds like the leader of your Youth Ministry needs to have her little rear end drug before the elders to explain her actions. Nothing wrong with helping the lady out, but at some point it becomes obvious that you are not actually helping her at all, just postponing the enevitable demize that her decisions will dictate. At that point, it is your responsibility to put your foot down. I've been through this before and had varied results. I've had very apprecitative elderly widows that could only say thanks, come in and have some fresh lemonaide, and I've had lazy slobs that wanted more and more. Many church leaders do not have the leadership skills required to address situations like yours. Biblically speaking, you are just as qualified as they are to address the issue on the spot, and I have found myself having to do exactly that, if for no other reason than it's my tools, and my equipment, and the Lord put them under my stewardship for a reason. Besides that, it's my gift, and I'll give it to whom ever I see fit. When she came out and swiped a pizza, I would have taken the youth leader inside and explained to the home owner that according to biblical principals, it is HER responsibility to be OUTSIDE, PARTICIPATING in the clean up process. Even with a medical condition, she can get off her spoiled, lazy rear and pick up sticks or rake leaves. Sure, when she gets hot and tired, she can stop, sit down, and take a break OUTSIDE with the rest of the workers. I'm used to showing up at a project and working a lot harder than anyone else. It's my nature, and I'm okay with it. I'm not okay with advancing the wellfare state, and I will not tollerate the group of believers that I associate with doing it either. I recognize that a lot of times we do things like this in an effort to build a relationship with the person that will give us the grounds to minister to the more important needs. However, first a person must desire a change in their life, and in situations like these, the person is perfectly content letting someone else do the work. Someone else did the work for me 2000 years ago. The bible teaches that we have a debt. We were bought at a very high price, and we are to live accordingly. Situations like this teach people to do the exact oppisite, to accept the gift as though it should be expected.
I recognize that you are not looking for sympathy with regards to the home owner, and you are right. You don't deserve any. You did a good deed, and that is it's own reward regardless of the character of the recipient. I do feel sorry for you in that the leadership at your church (like many others) is seriously lacking, and is apparently NOT accuratly teaching biblical principals to its members. My hope is that you are able to constructivly address this with your leadership.
Mark