I think that people who don't know if a planet is closer or further than a star...
...should not buy a telescope at all - and they certainly should not invest a lot of money in one.

Astronomy education needs to start somewhere where you have a chalkboard or piece of paper. And it needs to start with a bit of history.

I agree.

I would also toss in a bunch of photographs of galaxies, sequenced to end with spirals resembling our own galaxy. Then move to a diagram of our solar system's place in the Milky Way (like the one on my "You Are Here" sweatshirt), and work the distance scale back from there.

Then take them outside to look back out at our galaxy, conditions permitting. Then comes the history: leaving proper motion or the precessions of the equinox and celestial north for another time, I would remind them that people on Earth have been looking at the very same sky -- and wondering about it, making up stories about it, and using it to tell time and direction -- since at least we could be labeled H. sap., if not earlier. Call it a million years to be safe, during which time Sol has moved less than half a degree in its orbit around the galactic center.

Lesson 2 is the "we are stardust" lecture. The life of stars, supernova nucleosynthesis, dust cloud enrichment, and stellar nurseries (profusely illustrated, of course, courtesy of Hubble... but leaving out the H-R diagram), Moebiused back around to our own constituent elements. It ends with my rant about people (some of whom I've met) who quail at the "insignificance" of Earth, mankind, and themselves in the face of all that distance, time and chance. I reply: the fact that I, and millions like me, can not only grasp but embrace the enormity of it, and understand something of the physics and chemistry that makes it work, and keep it in our heads to contemplate, does not make me feel insignificant at all. Exactly the contrary: it makes me a peer with the universe, and all that's in it.

Only after a sense of place is established is it time to learn about what's in the neighborhood and how to find it: conventional star-chart astronomy, always beginning with naked eye. And I'd begin as I taught myself: the brightest stars and their spatial relationships among each other, bringing constellations in as a secondary topic.

For years, I've had the bug to write an intro astronomy book ostensibly for young adults of the future, living in Earth-orbital and Lagrangian colonies -- for whom no horizon obstructs their potential view of the entire volume at any time of year, except the part occulted by Earth of the Moon at the moment, or obscured by solar glare*. I'd use a perspective looking 'down' on the Earth/Moon system and the stations' orbits, easily extendable from there to the ecliptic plane and the planets as other bodies in orbits...

In short, an instinctively three-dimensional orientation. We dwellers on planets have a hard damn time overcoming the two-dimensionality of the overturned bowl which turns above us, rather than being on the surface of a sphere spinning within the sky.

[* -- The best time to observe (except if out at a Lagrange point) is while in Earth's shadow; as I see it, people would orient outward along the Sun/Earth axis... completely opposite us Earthbound types who tell time and season by where the Sun is, instead of where it's not. That outward look will draw them to live farther out, too.]