Originally Posted by
danseurderrick
If I were you I'd calculate when I'll hit lifetime Diamond via MM and only extend my Diamond status by that number of years (with some cushion) and convert the rest to miles.

It's not the worst idea. I have to figure out my strategy. I currrently average about $350k a year on credit card spend, so I was hoping to migrate a lot of that spend to a regular Amex card to have more flexibility in redeeming miles for longhaul J since DL's pricing structure is out of control. Essentially, we the 7 year stretch, I can remain diamond while being able to maximize J redemptions without having to worry about requalifying.
All fun things to think about!