(Free Nights Awarded ) Why I paid over $1000 to upgrade 3 no-fee Hilton cards without a bonus offer

I wanted to do a follow-up to this original post as there were some questions about whether notUpgrading to the Aspire would get you a free night award without having to wait for the next anniversary.

I upgraded all three cards at the same time. The three of them had different anniversary dates, but they were in the middle of the membership year. The credit was given immediately upon upgrade. All three of them were charged a pro-rated annual fee in the statement period after I upgraded. We received three free night awards after being charged a pro-rated annual fee and 6-7 weeks after upgrading.

After a no-fee card has been active for at least a year, American Express will often provide upgrade offers from the no-fee Hilton Honors card to the premium Hilton Surpass and the super-premium Hilton Aspire.

Because of this, it is common to avoid cancelling an Aspire or Surpass and instead to downgrade them to the no-fee card.

My wife and I had three no-fee cards that were all over a year out from a downgrade, but I upgraded all of them.

The best hotel card on the market can be a revenue- positive annual proposition. Here is a recap of what happened.

• No foreign transaction fees
• Hilton Diamond status
• $250 Hilton Resort Credit per membership year.
• $250 Airline Incidental Fee Credit per calendar year.
• One Weekend Night Reward at almost any hotel or resort in the Hilton portfolio with your new card and each year of Card Membership (currently usable any night of the week).
• Priority Pass
• Annual Fee: $450

If you can take advantage of the full value of the two credits, you'll get a free night worth up to 120,000 points each and Diamond status, which never seems to go away even after you downgrade the card. That is a good deal.

It's because we did not like the idea of extending the night certs. We decided to wait for an upgrade offer this year because there was no plan for a Hilton resort stay last year.

Ok makes sense, but then you did what?!?

Zemi Beach House joined the Hilton Portfolio and we were more interested in spending time on the Caribbean island of Anguilla. It's difficult to get to the island from the West Coast, so a short stay isn't desireable.

We were supposed to go to a conference in Germany the last week of March, but that was postponed, leaving us with an open week.

We'll get free breakfast at the resort and there's a lot of fun places to eat on the island, but I assumed we'd want to eat at least once at the resort. The Thai House Spa is a great place to have a few hundred dollars of resort credit.

Wait. A lot of people who read this site are saying that you spent $1350 to upgrade three cards in order to get $750 of resort credit.

My reasoning is here.

• I can always use the full value of the airline credits by paying a seat fee to upgrade cheap Alaska tickets (without logging into my account).  After 24 hours (so the charge isn’t refunded to the card), I can log in to my account, cancel the ticket for no fee and place the entire balance in my Alaska wallet for future travel.  The airline credits reset on the calendar year, so I’ll get a total of $1500 in Alaska credit before I have to pay another annual fee.
• Stephen (who saves us all money) confirmed that when he upgraded his no-fee HH card to the Aspire last year, he got a free night on the front end and another one on his first anniversary.  After researching it, I found that others have found this to be the case as well.  I dont know whether or not this is official policy and so it could end at any time.  But it seems as though, even without a points bonus, upgrading to the Aspire triggers an immediate free night cert.
• Officially you can’t keep your anniversary free night if you downgrade to a no-fee card, but in practice if you wait for it to deposit into your Hilton account and then downgrade, it will stay there.  Since Amex will prorate annual fees throughout the year (as opposed to the 30 or 60 day limit on most issuers), it might cost an extra $30-50 dollars depending on how quickly the cert is deposited.  But you’ll have a free cert valid almost anywhere.

In the first year, I'm expecting to invest $1350-1500.

• $1500 in Alaska wallet funds
• $750 in credit at Zemi Beach House
• 6 Free Night certs good for up to 120,000 points each (completely replenishing what we used for Zemi, but valid until into 2023)

It felt a little yucky to have to spend a lot of money at a resort that we will be at already.

Final Thoughts

As a follow-up to my earlier posts about trying to tailor our points and miles earning/burning towards both enjoyment and value, I wanted to talk through this whole process. The myth of one size fits all and Chase Sapphire Reserve is worth $250 for me.

This was another example in which I hesitated to make decisions that ran counter to how I thought. I don't think everyone should run out, but I had to think through it, as my first impulse was to say no.