As someone who is also woefully ignorant about telescope operation, this is what I learned while prototyping experiences during the October eclipse:
It's a lot harder to locate the sun with a telescope than you think. You can't look directly at the sun to try to site it. It moves, so you have to either have a tracking telescope or manually move it. It takes some figuring to find a scope with the right barrel length so you can get the whole sun, including the corona, in view. We worked with the local Astronomical Society to manage a telescope, and I highly recommend using folks who work with telescopes regularly to manage a telescope. We purchased them an eyepiece camera insert so we could run a live feed.
If you want visitors to view the eclipse non-digitally, I recommend using sunspotters, which are easily adjustable and create a projection of the eclipse. They are much more expensive than a cheap telescope but infinitely easier to manage. We also landed on binoculars with solar filters (brand-name sunoculars come with builtin filters) as the easiest magnified view of the sun for visitors as it is much easier to find the sun this way.
I recommend building one Sun Funnel per telescope and then having a feed pointed at the projection. It should be an easier set up. If you're looking at telescopes, be sure to order your filters for them asap.