I like the teleport system, but it would make more sense if you had to walk to the nearest teleport site to use it. I understand why they don't work like that because I think the game assumes that you DO that travel and just makes you skip it as something that would be a bit of a slog otherwise. So, I too suspend disbelief and accept it. Of all the things that could be changed for the better, that would not be something on the top of my list. JMO.
Somewhat yes and somewhat no. You can interpret the game as assuming you actually DO that travel, but it doesn't actually check. E.g., you can fall down the spider hole to the underdark with no way back up and not having found any underdark waypoints, and still teleport out. Even though the path you'd take find the nearest waypoint would likely lead you past an encounter.
I'd prefer if the game checked the autopath to the nearest (known) waypoint and either interrupted this movement with an encounter that you trigger or said "no path to waypoint" if it was impossible to manually walk+jump to it. This would be the best of both worlds - the occasional tension of having delved too deep for your safety combined with removing the slog of always walking back to a waypoint.