We sent them to college then changed our name, address, and phone number
A couple days after I started at USNA, my family moved from Pittsburgh to Denver. (They gave me their address.) So when people asked me where I was from, I said Pittsburgh. When they asked me where my parent's address was, I said Denver.
USNA databases would only deal with one address, and they picked Denver. So that dichotomy led to a number of interesting conversations with people who I was eager to avoid conversing with.
It was kind of open ended. I'm just wondering how tough it is for people to retire before sending their kids to college.
It's "just" a matter of how much money you want to spend. If you want to sacrifice ER for a few years to put your kid through college then it's a personal choice and a budgeting/saving challenge. By "personal" I mean "the sense of internal satisfaction derived from behaving in accordance with your values", not "your kids will thank you for it".
In 1992, when we'd procreated but hadn't thought much about ER, we bought into the conventional wisdom of paying for college. We started with the College Board's survey data, applied their college-inflation rates on the spreadsheet, chose an assumed investment return, used our TI calculator decision-making handbook to determine the monthly savings rate, and began saving $100/week to meet the 2010 goal. This was before 529s so we used EE savings bonds for a year or two (while they were still a good deal) and then shifted to a UTMA split 50-50 among domestic & global value mutual funds. I'd update the spreadsheet annually from the College Board survey (later their website) and we later started setting aside $5K at the beginning of the year.
This worked out great during the world's biggest bull market. It didn't work so well during 2000-2001. About that time I became aware of Buffett and book value. We ditched the domestic value fund (Heartland Value) and bought Berkshire Hathaway. I ER'd in 2002. We continued to ride the global value fund (Tweedy, Browne) until about 2006 and Berkshire until early 2008. We've been sitting in CDs for nearly 18 months.
Then our kid decided to apply for an NROTC scholarship. Woo-hoo! The recruiting district just put her in for an immediate scholarship reservation, which should help persuade Rice that they can afford to admit her. The money's still sitting in CDs in case NROTC doesn't work out. Whatever's left over will be strongly nudged toward her Roth IRA (and the TSP if she stays Navy) and the rest will discharge our parental obligations of helping her to come up with the down payment for a post-Navy house or for funding her own kid's college expenses. We're legally obligated to explain to her how a UTMA works, but we're not legally obligated to do it before she turns 21.
If I was doing it all over again, I'd use a 529 with a goal of paying for four years at UH. Everything else would be her problem.
Then from May/June things changed.
This summer, while our kid was at a three-week college program, I learned that Facebook has a feature to indicate whether or not you're in a relationship. Has your son recently been flipping the setting on his Facebook page?