My son will be out of high school when I am 41, so that wouldn't work for me.
My oldest started middle school just about the time we paid off our house; at that time we were able to begin to take some really great trips with our kids -- at the age they were really able to enjoy them!
That can go both ways, though. We know people who were all about planning for the future and now, as they sit in paid-off homes with cushy retirement accounts at their peak earning years, they wish they'd been less thrifty when their kids were small because all the money in the world can't get those years of working overtime/weekends and never vacationing back.
Ah, but you sound as if we didn't do anything fun in those years while we were making financial responsibility a priority. Without looking at our many scrapbooks, here are a couple things I remember from our "lean years":
- Friday nights when the girls were little, we'd get a bucket of Kentucky Fried chicken and meet Dad after work at the park. We'd eat a picnic dinner and let the girls play 'til dark.
- I used to be in charge of the prom, and my girls were just hankering to go. So my husband would go over early with me (being a chaperone, I always had to be there early), and he'd bring the girls. They'd dress up and he'd get them each a flower. They'd dance on the empty dance floor (they didn't realize there was no music) and snag a cup of punch. Before the high schoolers started arriving, he'd take them out to a special daddy-daughter dinner -- they always chose Pizza Hut.
- We did so many craft-y and cooking type things with the kids when they were younger. Things that cost almost nothing: For example, we don't get snow much, but we used to fill squirt bottles with food-coloring water and paint masterpieces out in the yard. The kids still talk about that. And we used to make these massive doll-apartments out of gallon milk jugs -- we'd add onto our monstrocity every week. So many things like that.
- We have family that lives at the beach, and many times we've packed a cooler full of sandwiches and gone out for a couple hours of night fishing. It was great to be the only ones on the beach.
- We started them camping in the backyard, and then "moved up" to real camping. One thing they used to really enjoy was camping on Halloween weekend, when all the campers at the state park nearest us used to bring pumpkins and have competitions.
- All our memories from those years aren't good. I remember once we took a wrong hiking trail, and we had to push the girls beyond their endurance level. By the time we realized our mistake, it was better to keep going than to backtrack, but we were very afraid of being caught up on that mountain after dark without food, water, and adequate clothing. That was bad.
Do you really think my kids have no special, unique memories of their childhood?
Spending more money
does not equal better memories. And you're ignoring the benefit to the kids: In middle school and high school their travels have been more frequent and more diverse than those of their friends (since we live on the East Coast, few of their friends have seen the Grand Canyon and I don't know anyone else who's been on a buffalo safari). We can write a check for each of them to have a
new car to take to college. They won't need to concern themselves with student loans, and they won't need to support us financially in our old age. Is this worth the trade-off of having done lots of camping and family-visiting in their earliest years? Yep, sure is.
Living frugally and saving in our early married years was the best choice we could've made FOR OUR CHILDREN as well as for ourselves. Rather than shorting them in any way, being frugal has allowed us to give them much more.
That's us too. When I'm 40, we'll have two in college. If we'd stayed in our old house that's about when we'd have gotten the mortgage paid off - 12 years ahead of schedule on a fixed 30 year loan - but there's no way we'd forgo vacations for our older kids' entire childhoods to accomplish that a few months or years earlier.
When you say it that way, it sounds extreme. When you look at my reality, it isn't. We lived frugally so we could pay off all our debts before we were 40; I do not anticipate borrowing for anything again ever. And my kids have had LOTS of vacations. They just didn't have traditional, expensive, stay-in-a-hotel and spend money vacations in their earliest years.
I'd rather die with a heart full of sweet memories rather than a bank full of money.
Why do you assume it must be an either-or situation? Why not have both?
I am now almost 30 and growing up we could only afford day trips. Once we spent 3 days at a hotel with an indoor pool and I thought I had gone to heaven
I have great memories of those trips and my husband and I still love day trips!
Yeah, we did lots of that type of thing when the kids were smaller! We went with my husband on a number of business conferences, which was free except for our meals. And a number of times we took the kids to an inexpensive hotel mid-winter so they could swim in an indoor pool.
I love Disney like all the posters here - but like all kids - my kids really preferred the Pop Century Pool to almost every thing else on our last trip... We would get up in the morning, get out the door to catch the bus for rope drop, and we'd be just arriving at the Magic Kingdom and my kids were saying, "When can we go back to the pool?" 
