Orient vertically for a crisper stereo image. Generally it’s recommended to put the tweeters on the inside.

Trueplay after pairing. The pairing process actually erases any previous tuning. 

Thanks @ratty ratty.  I should have mentioned (not sure whether it matters or not) that I have a rather large area to cover with these two speakers.  I have an open floor plan so the speakers are covering an open space of about 3 - 4 rooms.

In that case, experiment.

Orienting vertically, but with the tweeters on the outside, would widen the soundstage but possibly at the risk of wall reflections. Orienting horizontally would also broaden the spread, and may be appropriate for your needs, but at the expense of a more diffuse stereo image.

Question:  If I turn my stereo paired Fives Vertical do I need to redo the Trueplay or does it not matter so long as I’m leaving the speakers in the same spot?

You should do a Trueplay retune. The speakers work differently in the vertical orientation. For example only the centre tweeter is active. The acoustics will therefore change. 

I seem to recall that the system may detect the change of orientation and cancel the previous tuning, but I can’t be certain.