Can you elaborate on how your outbound flight upgraded a few weeks in advance? Was that due to your SWU and going forward your only hope for the M fare would be to upgrade at the gate with 25k miles? Nothing would happen in advance?

You got it and thank you for taking the time to provide your insight.

These are good points as I do usually book far in advance and at the lowest rates possible. The bottom line is that I am going to fly either way so this is why I'm undertaking developing a personal strategy. As I mentioned the old strategy was "cheapest & meets my schedule" which worked but provided no benefits. At least by just holding the Amex I board in zone 1 now. Winning! (ha). By aligning my stars with Delta there is at least a chance of upgrade benefits. Again, for me, it's not even that big but to just have a chance seems delightful. I don't even do tons of domestic travel. One of the biggest appeals of the "unlimited upgrades" is that it also applies to travel to the Caribbean which is where I travel most (historically). We were fortunate to have spent over 30 days in Jamaica last year over several trips.

I was thinking as a GM I might have a pretty good shot at an upgrade on a flight to MBJ (non weekend) but perhaps you guys can level set me there. I assume that is a not a super frequent place tons of DL and PL are going all the time as it's more of an exotic location. But hey, everyone vacations and I'm sure there are plenty of FF who travel between US and Jamaica constantly for work.

DM is the status that attracts me the most with the GUC's but that will just not happen until I can sustain like 220k a year on amex's. Once I can.... it's on!

Status really just helps. Since I'm flying anyway I might as well collect points. Clearly the big skymiles earner in my strategy would be via the Amex card. What other ways might I be missing (outside Skymiles shopping, dining etc)?