I definitely understand the pressure family can exert on financial issues.
I have a sister who has made several choices, mainly dropping out of school to work another job to support a high-school dropout who does not work. Married said overacheiver at 22. Decided that working is hard and paying rent is for stupid people, so left a decent paying low skilled administrative job to 'nomad', Ie: couchsurf, usually at friend's homes who are 'stupidly' paying rent, or poor relatives in Section 8 housing (Benefits that could be lost with two people not allowed to live there long term. Thanks for taking on risk for me, Grandma!) She regularly asks for handouts from members of my family - car insurance payments, gas cards, small amounts of money for food, car repairs, a used car, "That you don't need anymore." Ect.
The relationship is strained whenever any of these choices are questioned and if you are responsible finiancially and don't wish to enable this scenario, you are a souless zombie with no soul or appreciation for 'art'. Basically, it's fine for me to work for money, as long as I share without question, but they are elevated and enlightened beings who are above such things. Money is for wage slaves, the universe provides me with abundance...blah blah blah!
On husboo's side, he has a *very* irresponsible and grandiose father that's has been bailed out with over 30,000 US over the years (lives in a country with a very favorable exchange rate), fled a different country to avoid debtor's prison, likes grand and expensive parties and events that he can't afford and puts intense pressure on his two sons who are just getting established to fund them.
Wants to start a glamorous restaurant instead of expanding with profits. Unknown profits, that is, but you should invest on the ground floor for 40,000 without seeing a balance sheet that isn't napkin math and doesn't know his losses/profits or labor costs. Bank won't approve a loan and we would qualify for a lower interest rate. How dare you question me about how much debt I have! His only problem in life is that no one has ever believed or supported him.
My general rule of thumb has been to give without condition only if I can do so without wanting to get involved in their life choices. Which, for these individuals, is almost impossible considering the amount of history and actual money that has disappeared and not really changed anything.
I have offered to pay a year of interest for a loan that they sign for to start a business to both of them. Neither took me up on that, even though the interest would be around 14.9% for an unsecured loan with awful credit.
I did help a brother with a downpayment for a rental property and one years worth of textbooks for another brother, but that worked out just fine. Only put as much effort into helping improve a situation as they are, otherwise the momentum and risk is all on you.