You painted many scenarios here which is fine but let me comment on the family members

It's true that some are money drainers...I have one in my husband family who will always seek for financial help 1001 times
No matter how much u invest in him, he will squander it within months and come back for more

At a time...we set boundaries.. became strict on him and he adjusted

Some people are just lazy and I won't help them to keep on being lazy