I am in the same boat. I am Hilton Diamond, MR Plat, and SPG Plat. I have just re-qualified for Diamond with Hilton and Marriott Plat. But I'm trying to decide whether to continue on with the Marriott promotions, which are pretty good right now- or to requalify for SPG. I will requal for SPG gold with a few more nights. But to requal for Plat will take a lot more commitment. However, I have not had many opportunities with SPG this year because of where I've traveled to, unfortunately. But I do really like their program, and I agree that they tend to value their platinum level far more than Hilton. I think Hilton pretty much sucks these days. Yes, they tend to hand out more points, but it sure seems to take a lot more to get the free nights. To me the best part of Hilton Diamond is the free breakfast, but that's the same as just getting Hilton Gold. So I really don't see a lot of value in being a Diamond. If I were you, and had the choice, I would do what was said- ask for a challenge to SPG Platinum and then make the switch. And SPG just released their new promo for Q4 which will be triple starpoints for stays of 3 nights or longer (double for stays of 1 or 2 nights). That's probably a lot better than anything Hilton will offer. Just make sure you check the list of hotels that are not participating, to ensure the Sheraton you are staying at is participating. And then push the Sheraton to give you bonus points for staying there. I think that would be the best decision, and I think you'd really enjoy the benefits of becoming a platinum with SPG. Just my two cents.