Hello Sean, from a technical standpoint does it appear that RIG and DO are in fact making a turn or is it still to early to tell? Thank you

Yes, RIG and DO have improved technically as oil has been strengthening and hitting new 52-week highs. DO is leading the way so far for RIG to go (technically on the charts).

If someone is really high on DO, should they average down.

As tempting as it might be I would say the fundamentals do not suggest putting more money into it (or speculative money only).