As I understand it, if I generate a playlist, it will be in the same order as the imported folder / album...if I want a randomised playlist, should I simply randomise the order then generate a playlist, will the playlist then have the tracks in this random order. Also if I have several albums imported, then randomise then click on the album header, then generate playlist, will that result in random playlists for all the albums individually. Not sure how else to randomise playlists for multiple albums in one go, maybe in generate playlist, it could have a checkbox to randomise 
As you have thought of so many methods and possible approaches:
which of these have you tried and with which did you get the best results for you?
IMHO most of them are possible ways - but I cannot say if you would be satisfied with the result.
The randomization function in "Generate playlists" is probably something that will collide with the purpose to generate various playlists from a set of files but not a single one. For the generation of a single, randomized playlist, the function File>Playlist (of selected files) is much better.