Hero, that's the right attitude for sure.
Just because a farm is worth a lot more now than it was back then, that doesn't mean that it would have "paid" or "been wise" to have bought it back then. The added debt on a farm in the 60's, when coupled with the lower yields of the times, and the lower prices, may have just been able to service the interest enough to keep the banker at bay. A 15 year loan in the mid 60's would likely have ended up having to be refinanced in the late 70's to early 80's... would that kind of interest at that point have sunk the whole works? Would life have been "more stressful"? We could run these kind of "what if" scenarios all day long, but in the end, NONE of it is really going to matter much. We're not put here for the sole purpose of "gathering wealth".......... we're supposed to have a longer term "soul purpose"............... and what we do while we're here is really supposed to be just a means to accomplish that.
As for leaving "a legacy", or passing on "a large inheritance", how many of those have you seen where a lifetime of very hard work, getting by on little and making do without, smart business decisions and fortunate timing were quickly squandered by the next generation that got it handed to them? They weren't the ones that had to do all that hard work to build up that "nest egg"... so not only did they not "appreciate" the value of it, they had NO CLUE as to how to manage in order to maintain it. They hadn't had to put in the "hard work" that it took to achieve it.
Anything that you have is only valued as much as the recognized effort that it took to achieve it. THAT is what determines the "value" of a dollar (how tightly we hold it before letting it go)... the effort and difficulty it took to achieve that dollar (and I don't only mean to imply ONLY sweat and physical effort... just the fact of recognizing just how difficult it can be to "grow dollars", and how easily that can be thwarted by just a few stupid choices or lapses in frugality, is critical "work" as well). Give someone a dollar (think government checks, and I'll include the government welfare checks that we get from the FSA programs), and those dollars typically have a greatly diminished value in the eyes of the recipient.... People automatically want to run right out and buy that 72" TV or the 100 thousand dollar truck that was mentioned above, or that "shiny new tractor or combine" they drive by every time they go to town. If you have to work for it though, it's no longer nearly so much like "free money". When money is flowing in freely without much effort, it will also be spent freely, without much thought or concern for future need, unless the "hard work" of actually LEARNING these important lessons has been done. When money is difficult to achieve (there's the learning), it also will be spent much more wisely and frugally, and much more of it will be "saved for a rainy day", and more scrutiny will be applied to investing it wisely so it will continue to work for you on its own.