How about who has the poorest?
My family's always been pretty dang lower middle-class. Nothing to write home about whatsoever.
Dad makes good money now... but I'm also well on my own, so I don't really see any of it. Growing up, he made a very modest amount, was always between jobs, because the companies in his line of work kept going out of business during the 1990's and he'd be laid off or have to switch companies seemingly every couple of years. At one point, he even had to take a job in LA, and fly to and from it to the office every weekend (unless the job called for him to be in Northern California or somewhere closer at least). There was a lot of time not seeing my dad when I was growing up during that time, so It's still a special thing to see him. They tried to sell the house for about a year to move down to LA, but right when they got an offer on the place, Dad was laid off, and took a job at another company nearby, which ended up giving him real money for once.
My mother, who never went to college (I'm the first on my mother's side to go to college - ever) Worked a pretty dead ender at a credit union, working long hours for not much pay for over a decade, just to make mortgage on a sub-100k house (that's still nowhere near paid off, and the mortgage is in year 24 now). Mom now doesn't work, and with her financial services background kept us pretty well afloat in their starter home that is in one of the hardest hit counties in the country when it comes to foreclosures. My family has never had a new car. I grew up shopping at salvation army and goodwill and still do (Seriously, I find some kickass shit there).
Oddly enough, my grandma and granddad have 2 paid off houses.. one that they rent out. But their rental house is in the ghetto (seriously there was a murder 20 yards away a few years back, the house across the street is boarded up and graffiti'd all over with mexican gang shit, and the park nearby is a drugdealer's haven) so I wouldn't call that the most impressive, and it's hard to find renters that give a damn - might be more trouble than it's worth, and I doubt it's gone up in price.
As for skiing, I never had a new pair of skis until I purchased a previous season model back when I was 17 - they were always ski-swap deals growing up, and my poor brother always got my hand-me-downs until he bought his first pair at about 17 himself. My father was such a 1-ski-at-a-time-for-a-decade kinda guy, that he didn't get a new pair until he finally caved and took a pair of powder skis from me a year or 2 ago. We seriously ski-bummed it so much growing up (cheap hotel deals - sleeping in the back of the jeep, taking only daytrips) that it's 2nd nature for me to sleep in my car or on the floor - which is pretty damn helpful in that regard and I'd like to think it's toughened me up a bunch for that. We usually didn't even ski until March anyways, since it was way cheaper to ski then, the snow was always far better anyways, and that's when my dad would take time off. So we would usually only have about a 2-3 month season when it came to constant-skiing.
...anyways this is getting pretty damn long and apathetic but whatever. I'm stoked on my upbringing that we put all our extra dosh into ski trips and cheap fun stuff, rather than trips to the bahamas and expensive toys and houses.