Take my grandfather as a good example of your scenario, Cass -- land rich in Silver Spring come retirement, but short on money. So he just constantly got loans against the house to pay for the repairs and minor things, as well as post-retirement life, and it turned into a vast, sucking, horrible money pit nightmare... Selling in a frenzy as the market collapsed.
Granted, he made about a million bad choices. Maybe a million and one. But...that basic scenario was the root of the problem.
I don't know... I think it makes much more sense to build up a massive cash reserve instead of acquiring land. The goal should be to retire with at least a million of your own money socked away, plus SS and whatever else. While you're young, you can't enjoy the house because you're at work 12 hours a day and, when you're old, you just need one room with a hot plate and a TV and no stairs. So why bother?
I don't see rent as flushing money down the toilet, either. It's cheaper than 30 years of mortgage plus natural home disasters that end up costing you a grand every three months because a squirrel chewed on a wire or a toilet backed up and, just when you're ahead, your deck collapses or you need new windows and you're out 10k. In the renter's life, there's nothing to bring you down when you hit that "just got ahead of things" moment except for your own hubris (e.g. a publishing company). So, when you do just get ahead, you throw that money happily into the retirement fund!
I mean, god, a 30 year mortgage! Every cent I earn would be tied up in a house until I'm 64. Or, hell, if I need to refinance or take out a loan because the kitchen floor fell through thanks to a steady, undetected leak from the dishwasher, then it's longer than 30 years, isn't it? Next thing you know I fully own a house when I'm too old to work or fully enjoy it.
And when it comes to tax writeoffs -- start a company! I write off everything. Rent, utilities, the Nissan, my trip to NOLA, the cell phone, the internet, beers with girls...
That's one thing I love about running a company -- it buys and pays for everything. And the auditors are confused by publishing companies. "A month's worth of beer? Really?" *shrug* "Well, writers. They're drinkers." "Like Bukowski!" "Yessss... Can I go now?"