In all honesty, I don't see what the problem with booking engines offering oddball itineraries like the example you gave, provided that they give you the more direct and more reasonably priced ones first. If you scroll down to the bottom, why shouldn't it offer you all of the available options, as long as they are actually valid for ticketing?

I once found myself in BOS, needing to get back to IAH for a business emergency. I had missed the final CO flight of the day, and it was doubtful if I could make the AA flight that connected through ORD. I ended up making that one, but if I hadn't the only option on any combination of carriers that would have gotten me back to IAH in time was flying BOS-LAS on HP, connecting to the CO red-eye LAS-IAH. It would have been nearly twice the distance, and a substantial amount more expensive, but given my circumstances, it would have been the most appropriate choice. I'm glad that I was at least given the choice.