To avoid the possibility of opinions, let me rephrase the question. Which software packages are able to produce an Oblique Mercator map between any two arbitrary points, similar to what is offered in Matlab (see http://www.mathworks.com/examples/mapping/mw/map-ex21842716-create-long-narrow-oblique-mercator-projection) but without Matlab's price tag of thousands of dollars?
From what I've learned, Google Maps does not seem to work well at the poles. I'm willing to pay a few hundred dollars for the package if necessary, or I can put in the time to learn to use Geotools, GMT or whatever tool that can produce these types of maps.