Are there any issues with connecting speaker wire in this manner?

Doubling the 14 guage wire as you plan is inconsequential. For a typical setup 14 guage is fine! Now if you want to run 50-100 feet ...

Will this work? Perhaps only as an experiment. Stranded with banana plugs is really a better option.

Are you an electrician? Cause this is how they’d wire a light switch. I really don’t recommend anyone use solid core wiring because they are pretty brittle. They want to be put into a wall or conduit and left alone for 30 years. Every time you move them you break them a little.

Next, there’s the hardness of the connection at the terminal. Very hard metal to very hard metal here doesn’t tighten down very well. The lack of malleability prevents the squishiness that creates a tight screw-down terminal. Light switches have wire guides to ensure the wiring is flat to the contact plate and to the screw head and allow for quite a bit of torque.

The one area where I’ve seen solid core wiring used professionally for speakers was at Magico and then only on certain models and internally. Everywhere else they used Canare.

If you want to use AC wiring as an example to follow, look at how AC plugs and receptacles are built instead of how the in-wall wiring is done.  You'll see tight spring connections being used.

That is the way electricians wire an outlet when they want to do it best.  There are videos on how to do it.  make the loop fit tightly on the screw and orient it so that tightening the screw pulls the wire in rather than pushes it out.  if done correctly, this is an excellent connection.  

The solid-core copper isn't inherently brittle, but it work-hardens. Each time it is bent, that area becomes harder, and after being bent a handful of times, it will break.

Use stranded wire, strip the ends, twist them together well, then the form a U on the end to put around the binding post.