1. Mr. "I'll take 4 oxen and all the bullets $1600 will buy me" was amusing. At least he was amusing to me, Wifey who played the game as a kid also didn't see the humor, I think that was because every boy went the all bullets route at least once. Our results were invariably unsuccessful. Breaking down or starving to death way before getting anywhere near running out of bullets. You have got to allocate your resources to meet many different needs. All the bullets in the world will not feed you. All the food in the world will not help a sick kid. Medicine doesn't make up for not having a spare jacket or a broken axle. Prudent people allocate their resources diversely to meet their many needs.
2. To capture this significant issue in its own lesson; bullets will not solve every problem or keep you reliably fed. Sure you can hunt but even a great shot might not see game that often. You need to store food.
3. Sanitation and hygiene are important lest you want to die of dysentery. That pretty much speaks for itself.
4. Something will happen so you don't want to spend all of your money. If anything the game under emphasizes this point. You don't know what is going to happen. It could be running low on oxen or the need to replace that extra spare axle. People take cash so you better have some available.
5. People die and not just random strangers but people you know. The game made this almost laughable with like a 30 percent mortality rate but lets not ignore the point. To think that your family will get through a prolonged dangerous period without outside assistance is probably naive. [Especially if that time included multiple violent confrontations it is almost laughable. If you think some guns, maybe a bit of body armor and a day once in a blue moon in the backyard trying to do battle drills will mean you come out heroically and surprisingly and completely unscathed you're more optimistic than I am. Once you consider that these contacts are more likely to be defensive than offensive the odds get even worse.] Getting your medical training and supplies squared away is a darn good start. Being careful and using proper safety equipment is prudent also. Someone truly out in the hinder boonies probably needs to worry a lot more about a slip with an ax then a gunfight. However while I encourage you to prepare as fully as possible for all these situations it is worth squaring yourself up with the fact that someone could die.
6. Whatever the risk don't be afraid to seek opportunities. There are always risks in life. However if you refuse to pursue any opportunities because there is some risk involved you won't get much of anywhere. It could be moving to another state for a new far better paying job with some real potential or deciding to become a single income household. It might be moving to a rural home, into alternate housing or even off grid. All of these possibilities have some risks (though death from dysentery is low on the list) that need to be accepted. Don't be afraid to accept some risk.
7. Be prepared for a long journey. No matter how much you spend or how hard you work the road to preparedness, like the trail from Independence, Missouri to the Willamette Valley, is very long. Some times it is going to seem like it will never end but unless you keep moving the end never comes. Then you just end up in Nebraska or Wyoming which are nice enough places but much harder to farm in than the Willamette Valley.