Don't know where to start but the constant 'pity me' game my brother is set on playing is driving me round the bend! He and his wife have no kids, both work (not full time and not at a staggering wage but more than enough not to qualify as on the breadline), both smoke and drink very regularly (yes, my judgey pants are freshly laundered) but never have any money and constantly whine about it.
SIL's parents pay about 80% of the rent on their flat out of sympathy for them 'having no money' and the landlord is crooked as anything and hasn't even declared there's people living there so they pay no council tax, so they should have more than enough to live on.
DP and I on the other hand have a 3yo, are finding it hard to find ft work and get a decent income, find it hard to make ends meet but still make sure we do it comfortably. Because of this we don't have a car, don't go on 'proper' holidays, don't buy a lot of luxuries/expensive clothes/booze/meals out and so can save a little (miniscule amount to be fair) to cover emergencies and have enough to cover all we need, and now and then a little of what we fancy.
DB & SIL on the other hand spend money the instant it hits their bank account. SIL got a reasonable payout from a legal matter (she's fine in case I sound heartless) which quickly went on a few of their debts but mostly on a holiday to America, a lot of clothes and nights out. They've run up large debts on credit cards for lots of nights out and jet off to Europe whenever they've got any cash. Yet DB is virtually always moaning about how poor they are, and how stressed and depressed he is because they're so poor. He seems to completely fail to see WHY that is and thinks I'm managing because I get tonnes of benefits! Any time they need to spend anything to do with family rather than themselves (birthdays, Xmas, just coming to see us) DB launches into a massive spiel about how he can't afford it, is so upset, wishes he could treat us etc etc.
For my dad's 60th he couldn't even afford to put in £20 for a meal that had been planned ages and was originally HIS idea and rather than just bow out or borrow the money (I offered) quietly he went on for a couple of days to my parents about how poor he was until they cancelled the whole thing 
. More recently they spent out on a 3rd car (because they need one each and one is a massive 4x4 which guzzles petrol apparently) and then just a week later DB spent 90 mins on the phone to me whinging about one of his creditors taking him to court and how stressed he was about it.
I know these are only a couple of things but there's something like this regularly and it just grates on me so much. It's DB really, not SIL - ok she's creating the situation too but she keeps quiet about it, but DB has this permanent tragedy 'play' going on where he's such a victim because he's so poor and everyone has to be involved and pity him. If you even hint that he could take control and do something about it you're being unsympathetic and he'll go to the next family member who'll play along and agree you're being cruel.
I'm prepared to be told I'm being judgey and am jealous but can he not just grow up a bit? Oh and he's 7 years older than me so not a young student or anything. Without causing WW3 how do I make the point I'm fed-up with this game?