How/when to start “re-educating” a woman on her modern indoctrinations?
About the time she learns to speak. If she's not your daughter, this is not your gig.
What age to start a family at?
I wouldn't wait too late. Late 20's is pushing it. If you're a reactionary, you're not especially interested in wasting your 20's "finding yourself" anyway. You went into career mode not long out of high school. This plus your low time-preference and prudent judgement in mate selection means you're probably reasonably financially secure by 23-25. Prime time to start one's family life.
What age for a woman is too old?
Womens' ability to produce children has slowed dramatically by their mid 30's, and unbeknownst to men, so has theirs, if only to a lesser extent, and more in terms of genetic quality. Partner count is a reflection of character much more than it is of age, though one should grade this on a sliding scale; if she's 30 and has had 5 partners, that's not too bad, though one might wonder why she hasn't been able to settle with any of them; if she's 20 and has had 5 partners on the other hand, that's pretty bad.
If starting a family when they're older, how does one meet and court women who are significantly younger than them?
Don't let it get to that point. But if by some chance you have, I'll answers this and your first question, the answers to which are essentially the same.
Join a group related to something you enjoy. Perhaps something not unrelated to reaction. People of all ages attend these groups. Something maybe like fitness (health-conscious people are less likely to be promiscuous or have high time-preference), religion (obvious why this is related), or something technical (patience, focus, and persistence are key qualities here, and are more traditional values; e.g. engineers tend to lean conservative much more than HR workers). Having a wife that's pretty much a mirror image of your personality sucks, but by the same token, you need to share some values. Think of this as a sorting algorithm that may not be perfect, but is reasonably good at discarding people who are completely incompatible. It's better than a blind date. A side-benefit of this is that you get a chance to demonstrate in a group setting that you're preferable to other males; e.g. if you join a group and contribute value to it, you may be asked to chair or otherwise administer the group, which is an attractive position to hold, in the eyes of women.
Don't hide your views. Of course we all have to do this to some extent no matter what our politics; unless we're just numb to reality we probably believe something controversial enough to cause us problems. But if people don't know you're rightist rather than undefined, or worse, moderate, then you'll have problems in appropriate mate selection. Like attracts like. The fact is, there aren't many right-thinking women out there. But the ones that are out there, would prefer a man who not only thinks right, but is firm enough to wear it. This is essentially the rightist equivalent of virtue-signalling, but guess what? It works for the left, at least as far as attracting like-minded individuals, which is exactly what you're trying to do. In not hiding your views your circle of friends may not be as broad it otherwise would be, but it'll be much deeper; your friendships will actually be worthwhile. This will have a doubly salutary effect: not only will you attract more right-thinking women toward you, but you won't feel obliged to waste time on useless people.