Horrible Skymiles Redemption

I generally book flights on two airlines out of Boston: JetBlue and Delta. Together, these airlines comprise roughly half of the domestic travel at my local major airport (JetBlue controls 34% of the domestic market, and Delta is 15%). I used to fly a lot of Continental and American, and while American currently has a larger share (22%) of the market (and most of my international travel has been on OneWorld partners), I've grown disenchanted with both airlines post-mergers. Delta has provided a much more enjoyable experience in the air, and also in the terminal (both in JFK and BOS I've had snacks and water rolled-out to the terminal). Since my daughter started eating solid food, she's loved fruits, and Delta's snack selection in Comfort+ has always had at least a banana left for us.

JetBlue and Delta have the lowest-valued frequent-flier currency of the major airlines (adding United to the three already mentioned). I've found JetBlue to be fairly consistently around 1.2 cents when redeemed for a standard-fare economy ticket, Delta has tended to be more variable with a handful of routes still offering about 2 cents a Sky Mile (east coast to LHR, CDG). Most routes are closer to 1.5 cents, and Delta has been clear that they want you to think of a Sky Mile as equivalent to a US penny.

I just effectively bought 20,000 Sky Miles for $860, or valuing Delta Sky Miles at 4.3 cents a piece which is almost twice the rate for which I hope to redeem them. Because of our young twins, we don't plan on flying much this year, and I won't be requalifying as Platinum this year. I've been putting-off selecting my Platinum choice gift from Delta, presuming I'd take the 20,000 Sky Miles, but in a rash decision to buy-up the BOS-ATL and DTW-BOS legs of trip I had forgotten that I still had Delta regional upgrade certificates as an option, which would have saved me the cost of upgrading those competitive legs, and also upgraded the legs from ATL and to DTW which may still clear even as lowly silver next year.