Will a columella lift/tuck make my nose look shorter and the tip less pointy? (Photo)

Based on your photos, it appears that your tip is positioned lower than the ideal female position.  When the tip is lower, it can cause an appearance of hooded or "hidden" nostrils.  When you smile, the alar base (insertion of the nostrils to the face) elevates which exaggerates this appearance.  If your tip could be angled upward a few millimeters I think you would have far better balance and proportion to your nose. There is a tendency for the tip to project (stick out) more with elevation so this would need to be offset with the method of tip repositioning.  Alternatively, the bridge could be elevated a bit to balance the more projected tip.  I am a big believer in structural rhinoplasty, particularly in revision surgery.  Using cartilage grafts taken from your nose, more support can be added to the tip to allow for elevation.  You may find some of the information in the video link below to be helpful to you in understanding the balance of the tip and bridge in profile aesthetics.

A columellar-plasty can be performed when the columella is hanging. A hanging columella tends to make the nose  look bottom heavy and too long vertically. The columellar-plasty involves trimming back skin and cartilage on the caudal septum to bring the nose into better balance. This can be accomplished with the closed rhinoplasty approach with all of the incisions placed on the inside of the nose. For  many examples of  columellar-plasty, please see the link and the video below

There are a variety of issues that if corrected should make you more happy about your nose.  Yes, lifting the tip itself (less so the columella, in your case) would help to rotate and shorten your nose.  Additionally, some maneuvers to narrow the tip would be helpful. The area above the tip (the supratip) remains full, as well.  I recommend that you seek consultation with a rhinoplasty surgeon with vast experience in revision rhinoplasty.  Best of luck to you.