OK, I've worked in advice and welfare rights for the past 10 years and before that had the sort of "chaotic" lifestyle that would qualify me to be your client. I'm going to give you as honest an answer as I can. There's several reasons why your clients don't seem to be helping themselves:
1.They might be making rational economic choices that aren't obvious to you.
In your first example, a woman had got pregnant despite being homeless. If she's in temporary accomodation, the rent is likely to be much higher than either normal council housing or private rentals. It's actually not a good idea to have a job and be trying to pay your own way- almost all your money would go on rent, leaving you nothing to try and get yourself out of the situation.
The best thing is to stay on benefits, let HB pick up the tab and sort your life out properly once your settled in a council place. A new baby doesn't interfere with that process at all and might actually lead to a more stable income by entitling you to Income Support and getting you away from the sanctions regime. Poverty has its own economics.
- Stressed people make more mistakes.
If your going to drop and break your phone, you can bet it will happen when your waiting for a call about your crisis grant. Because you are stressed!
- You might be the strategy.
They might have factored in the help you are able to provide and concluded that this is their best option for resolving the problem. Therefore they are not making the effort to resolve it by other means.
- They wish to avoid situations where they will be made to feel shit about themselves.
Use the search function to find a thread about Health Visitors. See how much middle class parents hate being patronised and dictated to. Now use your powers of empathy to consider how working class people feel. Clue: They feel the same.
- Something else is going on.
Pp's have talked about people who feel the need to fill their lives with drama to avoid thinking about something more deep seated. I think this is very true. I know plenty of people like that. Sometimes the presenting problem isn't the real problem.
These are just some of the possible explanations. I'm sure there are more. What they have in common is that they are normal human reactions, not confined to "vulnerable people".
If your struggling to understand someone's motivation the answer is almost never that they are part of some special underclass that can't be understood or helped.