Originally Posted by IsleOfMan

I personally can't imagine shelling out ~$560 out of pocket for Diamond over Gold, even with the ~25% offset the OP might get from VS miles. The ONLY way I could justify it is if you could make property-hopping vacation out of it with enjoyable activities along the way (golf, sightseeing, whatever you're into), especially with an SO, though this would likely come with higher rates than what the OP has locally. A bunch of around-the-corner check-ins seem like a waste of money to me.

While Gold is indeed easy to come by these days, I don't think knowledge of such is quite so widespread that it's watering things down (at least not in comparison to the across-the-board devaluations). I've seen surprisingly good upgrades this year, even as Silver before making it back to Gold. Maybe the amount of time I spend at HIs and HGIs in the US skews my value of status, but even access to the best lounges I've seen in Europe 5-10 times next year wouldn't persuade me to shell out $500+ just to go from Gold to Diamond.

Making those nights worthwhile on their own, even if it thinly disguises a MR, might be a different story.