This is one of the best posts I've read through! It's helped me greatly in formulating my thoughts on my parents, and how their future is going to affect mine.
Dad - You've overcome a lot (years of drug addiction) to get to where you are now, but the backbreaking manual labor is wearing you out. You're 59 now, and don't know when you'll be able to retire!?!? Living paycheck-to-paycheck has worked for you so far because you've maintained your health. I'm terrified for when you can't continue. You've said that you'll get a pension in a few years, and with that and social security you and Mom will be fine. But when I asked how much your pension will be, you had no idea! You need to make a plan, and I'm happy to help. Also, one year of your life insurance premiums would be more than enough to pay for a funeral. Just save that money, and stop throwing it away.
Mom - Quit drinking. Like, seriously. You've had far too many serious health scares related to alcoholism, and you've seen this exact scenario play out before. Both of your older brothers, your Mom and your Dad, all died for reasons directly related to alcoholism. One or two drinks won't hurt?? Of course it does!! Also, get a job. You can't stand for long periods any more because you STOPPED STANDING EVER!! You complain about not having money, and that Dad doesn't do enough around the house, but he's working 50+hr weeks EVERY WEEK! He still makes dinner every time I'm over there visiting. You sit on the couch and nap, sipping on drinks throughout the day. I'm thankful that Dad does so much for you, but what happens when he can't anymore? And quit trying to get disability benefits. They're going to keep turning you down. You're not disabled. You're a lazy alcoholic.
MIL - You've been "renting" your sister's home for a decade, paying her less than the mortgage. She's truly a wonderful Sister, and I know she's happy to help you. Now, you buy a new car right after you've paid yours off, and you plan to retire this summer. If you have the money for this new car, and the money to retire this summer, why are you ripping your sister off? Oh, you're going to travel after you retire, so your sister can sell the house. Great! Wait... where are you planning to live when you run out of travel funds??? We don't have an extra room...
FIL & Wife - Thank you for offering to pay $4k towards our wedding. I really wish you'd have actually paid half of that, so I didn't have to get an extra credit card a month before the wedding to pay for the things you said you were going to. I guess it made it a bit more difficult when you had just spend $15k on your own wedding a year earlier. Also, you really could use a car more fuel efficient than your monster truck. Especially considering that you drive hundreds of miles each week. Your new house is beautiful. I hope it's cost reasonably matches your budget.
I kind of feel bad writing about my in-laws, because I obviously don't know their financial habits as well as I know my own parent's. Who knows, the in-laws could have nest eggs that I don't know about.
I'm actually going to my parent's house tonight for dinner, since DW has dinner plans with one of her friends. I'm going to show them my budget and plan for paying off debts. Hopefully my Dad will let me make a plan for them.