Hi Austin,
Regarding your 3rd shot that was way off the DR position.
AFAIK the sextant is averaging shots over the 1 min duration.
If the assumed position is far off the real position you will first have to pull up the sun into the bubble. Meanwhile the sextant is already averaging, so the first elevation measurements that go into the average are way off the real elevation if you're far from the assumed position, seriously affecting the end result. Sextant would show position closer to assumed position than you'd really be.
If you have taken some time to pull up the sun into the bubble during the 3rd shot (like 20 sec or so) that may be an explanation for the strange results.
I always try to have the assumed position not too far from the DR position (say, within 50 nm), and pull up the sun into the bubble as fast as possible (make a dry run shot and abort before the real shot to find where the sun is in relation to the bubble) to avoid such impact on the result.
Just a possible explanation. But I'm not 100% sure my interpretation how the gauge works is correct.
Btw, instead of getting position with shift-Z to get a new point of departure you could try to make three "star" shots at Azimuth 0°, 45° and 90°.
shift-Z as last resort
Good luck on your trip. Looking pretty good so far.
Gunter