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

Hello jdavis23401.  Your idea of using a double length of 14 gauge solid wire sounds reasonable to me. I use 14 gauge solid from my 300B amp to thier high SLP speakers.  It may be physically awkward, though. The idea of flattening the loop that goes around the amp's output post is a very good on. You want maximun surface contact between the post and the wire. Happy listening!

Emmetropia refers to great eyesight and hyperosmia refers to great sense of smell but if you have great sense of hearing you currently are considered to be an audiophile.  If you are blessed with any or all of these conditions, exploit them to their fullest extent regardless of what others think of your passion.  It's a personal thing !

I’m sorry but is this some kind of a joke?  Using solid wire for speaker connections?   You’re kidding right?  Why on god green earth would anyone run solid conductors for cables that transmit frequencies?   The more strands in a cable the better to counter act skin effects.  If you’re serious, don’t even consider it.  Run good standing pure copper zip cord.  

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.  

This is what I do with the 12-gauge single-conductor speaker wire I have running to my Maggies from my amp.  I have gotten in the habit or periodically reaching behind the amp to check the connection tightness.  Every few months there is a tiny, tiny bit of tightening that can be done.  I don't believe I ever come close to losing signal.  An occasional spray of CRC QD electronic cleaning spray doesn't hurt, either.  My listening room opens to the kitchen on one long side - and we cook.  A lot.  You'd be amazed at what a little electrical douching will do for SQ in such an environment.

@lcherepkai

Unless you’re willing to modify the chassis, run raw speaker cable internally, and direct solder to the exit points of the output stages, you’re going to be dealing some compromise in SQ. Each termination point introduces an additional "relay," contact point, inferior material, etc. into the signal path. But, us "consumers" want the convenience and flexibility of connecting things "easily."

While there is nothing "wrong" about connecting raw cable to speaker terminals, it’s not very convenient to do so, but certainly more convenient that direct soldering internally. And, depending on the number of predicted connect/disconnect events you see in your future, a direct connection (to the speaker terminals) may, in fact, be the most efficient connection method. The time spent terminating a cable so that it will be convenient to disconnect/reconnect later may be more time (and money) consuming than just connecting the cables directly IF you don’t foresee the need to move the cables for any reason.