My father regailed tales of his college years where it was a game to have a HAM radio operator start broadcasting and to have teams try to find where they were hiding, first.
More challenging? Not really. It does require multiple boots on the ground to do it.
Yes, more challenging. Ham radio fox hunting is usually VHF/UHF. Waaay easier to direction-find, since the signal isn't bouncing off the ionosphere, and also the much shorter wavelength means that you can get highly directional antennas that are small enough to be held, and don't need to be 50 feet in the air to work well.
Besides the problem caused by reflections and by the fact that unless you are very close to the transmitter you do not receive a direct wave but one reflected from the ionosphere, there is an additional difficulty.
Antennas with high directivity, which are needed for accurate triangulation, must be very big in the shortwave range (wavelength from 100 meter to 10 meter). Moreover, if they are too big it would be difficult to move them, to be able to measure an angle.
So traditional triangulation is inaccurate in this frequency range.
With modern technologies, using highly accurate synchronized clocks, one could distribute shortwave antennas over a large area, to create a synthetic aperture array, enabling a precise triangulation. However this would be expensive. An amateur would certainly not have such a thing. I doubt that even a state would bother to build such a thing, because it would not be worthwhile.
While precise triangulation of a shortwave transmitter from far away is very difficult, such a transmitter would not be hard to find during a local search wherever it is placed, because there not only the direction, but also the intensity gradient of the signal would allow finding it.
Two receivers of the same signal may not be from the same proximate source. One could from the original antenna the other from a reflection. Both could be reflected but by different reflectors. Even if the proximate source was the same for both the receivers, triangulation might yield the location of a virtual image of the original source.
BTW I am just going by geometry and may be way off because radiowaves behave quite differently compared to visible light.
One might need effectively the inverse of beamforming to nail it.
More challenging? Not really. It does require multiple boots on the ground to do it.