CliftonGK1

Same break every time at the 'inside of the wheel, left side'.

If I'm interpreting that correctly, we're looking at a consistent non-drive side break at the spoke head (by the hub, not by the rim) on the trailing (heads out) spokes.
That means that your spokes (especially non drive side) are seriously undertensioned, and since there have been multiple breaks and replacements, the entire wheel is likely true, but not evenly tensioned any more. If you have multiple broken spokes then the tension on the wheel gets more and more out of balance with each spoke replacement as the wheel is trued back up. Eventually, the tension is far enough out of balance that the only solution when replacing another spoke is to loosen everything up and start from scratch with tensioning.

As for fancy-schmancy wheels and spokes, they're nice to look at and in certain regards they're going to be better than some lower priced equipment, but it's not necessary. I've ridden all sorts of 32h wheels at weights up to 265 pounds. Anything from Alex DA16 rims on Deore hubs (stock Cross Check wheels) to replacing the rims on those with DT Swiss RR1.1 (now the RR465), a pair of 1991 Wolber T410 Alpine rims on IRO high flange track hubs with 14g DT spokes, and recently I've been using $15.00 IRO house brand rims on their $20 house brand hubs laced with 14g DT spokes. I don't run into any issues with spoke breakage, even on my CX bike that I take out and beat up on local MTB trails and jump my full weight onto the saddle after run-ups.