You are NOT (okay..I will admit that there are some cases where this might not be true for someone, and I really hope that's not the case here..) responsible for everyone else's personal situation. Help out where you feel comfortable doing so, but I think it's not right to not enjoy the things you've earned from hard work.
It's really easy for me to say "God damn, my situation sucks!" I live in a sub-1000 sq ft condo with my wife and 2 kids, it's really cramped, have tons of debt, a dead end entry level job, an achy back, have been sick all week, can't get any overtime this week or next week because holiday scheduling boned me at my job, have really *zero* close friends at the moment...this list of suckitude goes on and on, trust me. But you know...I don't really feel like anyone OWES me anything. I've spend my entire adult life taking care of my own mental and financial health, and I'm surviving. Lots of things were outside of my control, especially on the financial side. But you know...I'm not dying (that I know of? LOL...), I own some pins, have plenty of games and computers, my family, we just got a cat (cutting OTHER expenses to pay for that..you know..the responsible thing to do..), and I have a plan for this coming year to better manage our medical expenses.
Your money is not going to help your relative, unless it's highly conditional on them doing everything they possibly can for themselves first. I'm a firm believer that people have to find their own rock bottom before they will make the genuine effort to pick themselves up, do the necessary things and SUFFER through the hard times to make the future better for themselves. I was lucky...my rock bottom was far far higher than most people. My brother went to jail for a few years and has been dealing with a felony record. /shrug At the point he threatened to kill me, I didn't have contact with him for YEARS. I could not bear to close out my dad's estate and deal with his problems at the same time. He's had two kids by two different mothers, and one of them was worth enough to him for him to realize he'd had enough of being in and out of jail and crap jobs...he's running a Pizza Hut store right now. You laugh, but that little f'er is going to make more money than I do working for AT&T after 8.5 years this coming year most likely. He's turned his life around in a massive way, but he slammed HARD into the pavement before he figured out how to do it. We hang out quite a bit, he's turned into someone I *like* instead of someone that feels like a burden, and I'm really thankful for that.
It's my opinion the longer and the more you help this person, the less motivated they will be to solve their problems. Really the only time that you should go far out of your way to step into their business is if there is some immediate danger to their life, whether that's them having absolutely nowhere to go in terms of shelter or assistance, or mental health issues. And there's a ton of resources out there for both of those. But they have to want it. You're only delaying the inevitable, and you've already realized that in your own statement, I think. I saw the same thing with my mom and my brother. She tried to 'help' him for years, only to watch him destroy everything. It wasn't until he was truly left to his own devices that he fell far enough to do the right thing. He could've had YEARS more time as a productive human being, and MAYBE not have spent years in jail and with a felony record following him around had someone just been harder on him.
Just my 2 cents..which is probably not even worth 2 actual cents. But hey...