I'm pretty much in the camp that if it's a necessity, I'll help bail out my Mom, Dad, Grandmom, Granddad, Stepdad, and uncle. But I'm not going to help them live high on the hog.
Thankfully, my remaining grandparents (Grandmom on my Mom's side, Granddad on my Dad's side) are in good shape financially, and live well below their means. I really don't know my Dad's financial situation. We're not really that close, and I don't find it easy to talk with him about stuff like that. But he lives pretty cheaply. Dad also doesn't know squat about investing. I just found out on Father's Day that his savings plan at work (whatever they call the federal gov't's version of the 401k) is mostly in ultra-low risk stuff that doesn't pay crap. He keeps saying that he needs a computer to get online and change his elections, and he doesn't want to get involved because he wouldn't know what to pick anyway. Basically, keeping his head in the sand. I offered to help him out. My uncle doesn't know squat about investing either, so he lets me handle his 401k and his rollover IRA, from his previous employer. His only stipulation is that if I bankrupt him, he's coming to live with me! Anyway, I also told my Dad that more than likely, there's a 1-800 number he can call to change his investments, or request information, or at least talk with someone in HR. But my Dad likes to procrastinate.
My Mom and stepdad are pretty well off. She's on the old system with the federal gov't, so she'll get a fat pension when she retires in early 2009, at the age of 60. They have two houses, one up here in Maryland and one in Florida, and some property on a lake in VA somewhere. I was worried that they were over-extending themselves, but I talked to Mom one day, and she told me that when you combine both mortgages, plus the property taxes, the total comes out to about $1500 per month. In my area, that might get you into an apartment in a crack neighborhood, with all utilities included. You might even have your own washer/dryer, but will have to worry about your car getting ganked if it's too nice.
So, I think my Mom and stepdad are okay. They want to move to Florida when she retires, but she refuses to sell the place up here. Her reasoning is that if she hates Florida, she wants to be able to come back home. Unfortunately, she hasn't thought through far enough to the possible scenario of her hating Florida, and my stepdad loving it! She just said "Oh, we'll worry about that when we get to it".
In my Mom's case, I'd help her out if she really needed it, but I sure wouldn't help her hold onto two places, plus that lakefront property.
A few years ago, my Mom said something to me that, the more I think about it, seems kinda crappy. When I first mentioned building a garage, she said I should build a loft over it so that my uncle would have a place to live in if he ever needed it. Okay, my uncle is going to be 55 this year, and isn't in the best of health, so it's not exactly like Fonzie living over the Cunningham's garage. And more than likely, if it ever got to the point that my uncle was going to be destitute and needing a place to live, he's going to be even older and in worse health than he is now. Last thing he needs to be in is a loft above a garage! I'm thinking that's a hell of a way to treat your own brother, Mom!
The house I'm in really isn't that big, but it's big enough that it has a spare room that we don't use. I have two roommates right now. Biggest downside is that it only has one bathroom. But I figure that if I ever needed to house a family member, there is that spare room. And I could always put in a second bath if I had to. Or add onto the house.
As my grandmother's will currently stands, it's divided 40/40/20 among my Mom, uncle, and me. I'm the only grandkid on that side of the family. My uncle lives with my grandmother. I figure that when Grandmom's time comes, if my uncle still wants to live in that house, between the two of us we should be able to find a way to buy my mother out, if she wants to sell.