Well, like you said, we only win when we least expect it, so I'm thinking our odds are long.
(See how I twisted that around on you?!?)
Seriously, to me, it comes down to the fact that we will have to rebuild at some point. One can argue, we can win in 2021, too, and just keep "going for it," but it will involve more spending.
I see your point, and I've not placed myself in either camp, yet, but I do think that if we decide to reset and rebuild before and during 2020, we can turn things around faster and create a stronger roster going forward than by putting it off a year and maybe getting nothing for Betts and others.
It's a tough call. I'm about 50-50 but leaning towards beginning the reset now, because I think the 2020 odds are too long to be worth sacrificing the time and quality or the pending rebuild.