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How far is too far to aid someone?

NWRatCon

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Alright, here's my weird dilemma.

Background: I have a woman, 40ish, who comes to clean my house every couple of weeks. She does a mostly competent job, and, even though my wife, who originally hired her, is now living in assisted living and has her own housekeeper, I have kept her on. At present, I am her only regular client. I have no connection to her, except having hired her to house clean.

During the time that she has been working for us, she has gone through several emotional breakdowns, chemotherapy for a year, and experienced bouts of homelessness, living mostly in her car. Last winter I arranged with another friend for her to be caretaker for a probate property. She lived there about 6 months, and did a good job cleaning it up and minor repairs, but the trailer park refused to sign her to a lease. (That's a completely different bruhaha, with lawyer involvement, now.)

Over the summer, she again became homeless, and lived in her car until her son sabotaged her vehicle (he has his own mental issues) initially by stealing parts from it, and then sugaring her tank. So now she has no car, either. Until recently, she had a storage unit for her belongings, and they allowed her to use it as a backup shelter. She actually worked there as their cleaner (prepping units for rental, keeping the driveways clean and such), until last week when the place burned to the ground, and all her belongings went with it (she, thankfully, was elsewhere).

It was cold tonight, so I actually checked her into a hotel after work. I'm also trying to find her a new vehicle so she can get to other places to clean, and am exploring some Section 8 housing options for her. She has social anxiety issues and rarely makes it to intake interviews on her own. (I helped her get a phone and onto public health care, too.)

I just have a hard time letting someone I know descend into homelessness. When relatives and friends got into dire straights, I've taken them in. I can't do that for her, for a number of good reasons. My question is, am I trying too hard? What humane options do I have?
 
am I trying too hard?
Yes. Absolutely.

I went through something similar for near 30 years now. My case was more complicated but bottom line, be fair and compassionate even but don't go all in. They will become depend on you and it will really unfairly drag you down.
 
Alright, here's my weird dilemma.

Background: I have a woman, 40ish, who comes to clean my house every couple of weeks. She does a mostly competent job, and, even though my wife, who originally hired her, is now living in assisted living and has her own housekeeper, I have kept her on. At present, I am her only regular client. I have no connection to her, except having hired her to house clean.

During the time that she has been working for us, she has gone through several emotional breakdowns, chemotherapy for a year, and experienced bouts of homelessness, living mostly in her car. Last winter I arranged with another friend for her to be caretaker for a probate property. She lived there about 6 months, and did a good job cleaning it up and minor repairs, but the trailer park refused to sign her to a lease. (That's a completely different bruhaha, with lawyer involvement, now.)

Over the summer, she again became homeless, and lived in her car until her son sabotaged her vehicle (he has his own mental issues) initially by stealing parts from it, and then sugaring her tank. So now she has no car, either. Until recently, she had a storage unit for her belongings, and they allowed her to use it as a backup shelter. She actually worked there as their cleaner (prepping units for rental, keeping the driveways clean and such), until last week when the place burned to the ground, and all her belongings went with it (she, thankfully, was elsewhere).

It was cold tonight, so I actually checked her into a hotel after work. I'm also trying to find her a new vehicle so she can get to other places to clean, and am exploring some Section 8 housing options for her. She has social anxiety issues and rarely makes it to intake interviews on her own. (I helped her get a phone and onto public health care, too.)

I just have a hard time letting someone I know descend into homelessness. When relatives and friends got into dire straights, I've taken them in. I can't do that for her, for a number of good reasons. My question is, am I trying too hard? What humane options do I have?
Sounds like a "tar baby" kind of thing in that the more involved you get, the more you'll get stuck.
 
Alright, here's my weird dilemma.

Background: I have a woman, 40ish, who comes to clean my house every couple of weeks. She does a mostly competent job, and, even though my wife, who originally hired her, is now living in assisted living and has her own housekeeper, I have kept her on. At present, I am her only regular client. I have no connection to her, except having hired her to house clean.

During the time that she has been working for us, she has gone through several emotional breakdowns, chemotherapy for a year, and experienced bouts of homelessness, living mostly in her car. Last winter I arranged with another friend for her to be caretaker for a probate property. She lived there about 6 months, and did a good job cleaning it up and minor repairs, but the trailer park refused to sign her to a lease. (That's a completely different bruhaha, with lawyer involvement, now.)

Over the summer, she again became homeless, and lived in her car until her son sabotaged her vehicle (he has his own mental issues) initially by stealing parts from it, and then sugaring her tank. So now she has no car, either. Until recently, she had a storage unit for her belongings, and they allowed her to use it as a backup shelter. She actually worked there as their cleaner (prepping units for rental, keeping the driveways clean and such), until last week when the place burned to the ground, and all her belongings went with it (she, thankfully, was elsewhere).

It was cold tonight, so I actually checked her into a hotel after work. I'm also trying to find her a new vehicle so she can get to other places to clean, and am exploring some Section 8 housing options for her. She has social anxiety issues and rarely makes it to intake interviews on her own. (I helped her get a phone and onto public health care, too.)

I just have a hard time letting someone I know descend into homelessness. When relatives and friends got into dire straights, I've taken them in. I can't do that for her, for a number of good reasons. My question is, am I trying too hard? What humane options do I have?
You are doing wonderful things. Imagine if more of us cared about others like you do, what a wonderful world it would be, right?
 
An update. We secured her an operational car (at my expense) so she can now get to work, and she has a "summer cabin" that the owner is letting her occupy until spring. I'm helping her with applications for welfare programs, and she's on the list for subsidized housing. Moving in the right direction.
 
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