Obstacles:
When a ship or squadron overlaps an obstacle after
executing a maneuver, it resolves an effect that depends on
the type of obstacle it overlapped

So when I move my ship and it overlaps an obstacle when the move is complete - I suffer the effect of the overlap. Easy

If I trigger Engine Techs and I end up overlapping an obstacle again (same one or different), I would think that I suffer the effect of the overlap again. i.e. so I could hit two obstacles in one turn (or the same one twice it the base is large enough)

Correct?

Correct.

Perhaps, if using an MC80 with engine techs, you could manage to hit the same two obstacles twice?

Or maybe that's not possible, even at speed 1?

Perhaps, if using an MC80 with engine techs, you could manage to hit the same two obstacles twice?

Or maybe that's not possible, even at speed 1?

It's very possible. Imagine two obstacles distance 1 from each other and the MC-80 goes right down the middle trying to fit between and clips both of them.