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

I can’t see anything wrong as in dangerous in this.
 

I recommend you also go to Home Depot and get their 12/3 extension cord. Cut off the ends and try it as speaker wire in comparison to you solid core idea. A number of years ago one of the serious high end publications threw this in as a comparison with some low end solutions and it sounded really good. 

What you suggest will work fine.  As considerations:

• Not a bad idea to eliminate the spade or banana interface between the wire and the binding post.
• You can achieve the same 11 awg result by:
  • cutting the wires into the identical lengths you need to run from amp to speaker, while allowing a little extra for twisting (10%+ depending on diameter and frequency of twisting)
  • lightly twisting two identical lengths of the 14 awg wire together
  • stripping 1/2-3/4 inch at the end of each wire and then more tightly twisting the ends of the two twisted wires together, and
  • making a fish-hook shape with the twisted ends that can hook around your binding post
• Don't go crazy on tightening the binding posts (snug+ should be good) and they should last for a long time.
• You can further improve the "design" by:
  • using four identical lengths of the 14 awg wires which in your case is enough for both the +/- poles at each speaker (I assume you plan to use 8 wires total for two speakers, or 16 wires if you bi-wire?)
  • carefully twisting all four wires lightly to moderately together (like maybe 4-8 twists per foot) while keeping each wire oriented consistently with respect to the other wires (this is important)
  • untwist the last 6-8 inches of wire at each end of your "cable" to serve as the lead-outs to connect to your speakers and amp
  • take two wires that are opposite each other (not side-by-side wires) and twist the lead-outs of those two wires together and then do the same for the other two wires that are opposite each other, so you have now cross-connected the wires
  • finish the terminations as fish-hooks as discussed above and you will have one speaker "cable" (each cable made from 4 wires) that runs from the amp to each speaker
  • this creates what is called a star-quad geometry that lowers inductance even further than with twisted pair geometry, and lower inductance (along with lower resistance) is a good thing for speaker wire/cables
  • make a second set if you want to bi-wire  
• Having all four wires twisted together as a "cable" allows you to cover them with a single sleeve thus reducing the fragility of the bundled "cable" compared to having four separate wires or two twisted pairs of wires running from your amp to speakers. 
• Here is some noise reduction sleeving I like to use, otherwise I recommend the clean cut or even cotton, if your wire is cotton-covered.  You can then finish the ends of the sleeving with heat shrink and if you wish you can place red/black heat shrink over the lead outs for durability in handing and to make it easy to recognize pos/neg when you connect/reconnect your wires. 
• My favorite speaker cables continue to be made from solid core wire - yes, I believe I hear a difference.  I have some multi-gauge, multi-strand, high quality, solid core copper in cotton speaker cables I made that (IMO, wrt SQ) continue to beat anything else I have here, including several types of manufactured stranded wire cables using PCOCC conductors (Furutech and others I have tried).  The manufactured cables I have here that I like are from Harmonic Technology and those use multiple strands of multiple small gauge, solid core PCOCC copper in PE dielectric, with an aggregate of either 9 awg or 11 awg.

I believe you are on the right path.  Give it a try and tell us how you make out. 

Sure it will work.

 Have gone to Lowe’s and bought 12/2 Romax and it works fine and if you can, get some Banana plug.  They will make things easier in the long run.

All the best.

If you've read my recent posts on using slugs instead of fuses, then you may recall that I've been experimenting with metals less used in audio applications.  To this end, I'm considering trying molybdenum, titanium, and niobium wire.  The latter two are fairly cheap but the moly is pricey.  Also, I don't see any of these wires offered in bundles as typical of speaker cable thus, I'll be using solid core and, in my experience, solid core actually sounds at least as good as stranded wire.  

Without using spades or bananas, the binding posts on the Red Dragon amps are a PITA, and wrapping the wire around the post would seem to offer the tightest connection without possibly stripping the threads (which I've done).  I'm obviously not much of a DIY guy and just wanted to make sure I wasn't going wire the speakers up in a compromised or possibly damaging way.  I appreciate the information all have given.  Now to go on an exotic metals shopping spree......