Reply To: 2 Questions regarding modelling
To your first point: If you change the transform orientation from global to local it should work just fine unless you have applied the rotation. Pivot point can stay as median point.
If you have applied the rotation you can manually slide the vertices with g+g along the edge and if you hold alt you can go past the original position upwards. Problem here will be the destructively modelled bevel which will cause problems there. You could take the very top face and alt+e -> extrude face along normals and then drag the other vertices along one by one with g+g.
I might be overthinking this 🙂
To your second point: With those changing directions of the loops it is mostly unavoidable to have 3- or 5- poles. I learned that recently. You still have nice quads so some poles will always be there when you change loop direction. :/