Re: how high well does my boat point?
+1 on GPS track. But there are really two different things here.
One is your real track over ground which is a combination of sail trim and side slip. Side slip is helped by having more lift from your keel and to some extent rudder. Those are harder to correct although getting a good foil shape on the rudder helps and is relatively easy to fix/build. Keel is harder and you can only do so much especially with the type of keel the Columbia 26 has (It is a cutaway semi full keel right?)
The other is how tight an angle to the wind you can sail and still get power/lift and is affected by the sails, trim and shape, etc. To me the biggest/easiest thing to look at/correct is sheeting angles. The 26 with lifelines and the tracks out on the toerail (I assume) is not going to get you as tight a sail trim for the genoa which will definitely limit your ability to point. You could try running a smaller jib and adding a fairlead and cleat on the cabin top to tighten up the angle and see what that does. A traveler for the main will help too by allowing you to sheet in close to the centerline without flattening the main.
My 0.02 but there are guys on here who will definitely have better thoughts!