If the answer to these questions is more than zero then you are quite lucky. Most people have a family tradition that rarely goes past their great grandparents unless they are royalty or descendants of someone very famous.
In my own case the oldest object of certain origin is a pot made by my great grandfather Robert Douglas Marr at the beginning of his career as a potter. The oldest stories that have reached me by word of mouth -- rather than official records -- are more or less from the same period. From the records I know that Robert's grandfather was a carpenter named Andrew Marr, born in 1785, but no relative that I know has any stories to tell about him, nor do any artifacts survive. I suspect that he never gave any thought to the problem, but if he tried to pass on any messages they never reached me.
But suppose that you do want to connect with your descendants, the people you will never meet, is there any way that you can create an oral tradition that will survive beyond two generations? In a way this is related the crucial problem of media relations that you need to connect to your audience indirectly through other people. In other words you need to craft your messages in such a way that they appeal to the person you share them with but also encourage them to pass them on.
It is difficult to test techniques for this kind of long-term communications program, but here are some practical guidelines based on what has worked in the past for the generations before me, my three-step recipe for success.
1. CREATE STORIES. People remember stories much better than facts. Wrap your messages inside a memorable story and people are more likely to remember it and to repeat it to their children. The story should be simple enough to memorize and vivid enough to be retained after just a few tellings. If it needs to be written down it could be lost.
2. FIND OBJECTS. Stories are much easier to remember when there is an object that is there to remind you. It is also easier to tell someone to keep an object than it is to convince people to pass on a story. Never choose objects with a high intrinsic value or they might be sold, and better to label them, just in case people forget what they are.
3. FOSTER CULTURE. By far the most important of the three, you need to transfer to the next generation the idea that it is important to remember and to pass on the stories, the objects and also the culture of passing on these three things. Without this you might have a good story but not think of passing it on.
These are the three basic techniques for connecting with your descendants, though the details are a little more complex. You can try for yourself to choose and share stories, testing which are memorable. You can also identify interesting objects that support a story and make sure that your children know that you mean them to be kept, stressing the importance of passing them on to future generations.
If you would like test these methods in practice then let me know and I will message my descendants to check with your descendants to see how it went, and maybe revise this post in the light of experience 100 years from now.