Why Occasionally Upgrading to Premium Cards Makes Sense for My Family

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Like many of you, I had big 2020 travel plans that didn’t  materialize due to pandemic. We were supposed to go to Hawaii and Japan, and ended up driving to a neighboring state of Georgia instead. C’est la vie.

Since I like to plan everything well in advance, I was booking my Japan flights and lodging in 2019. After some research, it was clear that upgrading my husband’s Chase Freedom Unlimited to Chase Sapphire Reserve (in order to unlock Hyatt transfer) would make a lot of sense. See related post

Chase Sapphire Preferred would also suffice, but I figured that getting lounge access for an extra $55 would pay off, especially since CSR still covers airport restaurants.

Later on, I also got an offer to  upgrade my husband’s regular Hilton Amex (no fee) to Amex Hilton Aspire. This upgrade would cost us $450, but we would get 150k points+weekend night+$250 Hilton resort credit.  We were planning on spending one night in Los Angeles after our flight from Japan, and staying in Waldorf Astoria Beverly Hills was very tempting. Obviously, that didn’t happen.

Still, despite ruined plans, both of the upgrades proved to be very lucrative. In fact, far more lucrative than I ever imagined. Not only did I break even, I actually made money in the end. Let me break it down in detail.

Upgrading to CSR

Even though the upgrade was processed last June, the $450 annual fee didn’t hit until October of that year. I’m not sure why, but it probably has to do with when we originally got Chase Freedom Unlimited. Anyway, since $300 travel credit is based on cardmember year, that meant we would be able to get it twice before second fee hit. And indeed, that’s what happened.

I got $300 reimbursed last June, and another $300 this summer. The latter was valid towards groceries, a temporary Chase enhancement due to Covid-19 crisis. But wait, there is more! Since my upgrade, Chase has also introduced $60 annual credit towards DoorDash. We ended up using it towards an already planned date night, so it was almost as good as cash.

So, for $450 I got $660 in benefits, plus the ability to transfer points to Hyatt, which was my original  goal. Will I be renewing the card in October? No way. I’ve already collected  the benefits and don’t need to transfer points in a near future.

With how iffy 2021 travel prospects are at  the moment, I’m not at all certain I’ll come out ahead. So, the card will be downgraded to Chase Freedom Unlimited. I’ll have 18k points left, and will probably leave them be, until a good usage will present itself in the future. At that point I’ll upgrade again. Last time I did that, I got access to airline and hotel transfers immediately.

Upgrading to Amex Hilton Aspire

I made out like a bandit on this one, and it’s highly unlikely it will ever happen again. For some unknown reason, I got two weekend certificates instead of one. Hilton was aware of it, and I even got an email saying that I can keep the extra night even though it was issued in error. The certs are currently sitting in my account, but they are valid until the end of August of 2021. I sure hope I get a chance to use them eventually.

But the real value was in utilizing airline incidental fees. There are various, sometimes ethically questionable, ways to juice this benefit. I used it for its intended purpose, and bought  four  Main Cabin Extra seat upgrades on the AA flight from Japan to US. I made sure to utilize it for 2019 and 2020, since the benefit is based on a calendar year.

Of course, since AA cancelled the flight, I eventually ended up getting a refund of seat fees ( a total of $480). I should mention that I had to apply for it, since AA wouldn’t issue it automatically. Those weasels!

I also ended up taking advantage of $250 Hilton resort credit, and utilized most of it towards restaurants (a temporary benefit Amex introduced this summer). Thumbs up to Amex for working with customers who aren’t comfortable staying in hotels right now. My resort benefit was going to be wasted otherwise.

I found out via Amex chat that my fee will hit on September 30th, but the $250 benefit resets on September 3rd. So, I’m hoping to double dip on it. It may even be possible to prepay $250 in spending at a Hilton resort by filling out a form, and we do have a stay planned at the end of the year. I’m not sure I’ll go that route, as I’m hoping that Amex will extend the option to use it on restaurants. Developing…

So, in exchange for $450 fee, I got $730 in benefits, two free nights, plus 150k points (so far). Will I renew the card at the end of September? It’s highly unlikely. Yes, I could get another Hilton night that will be valid for two years, plus possible resort credit. But I’m sitting on so many hotel certificates at the moment, having another one isn’t even a little bit tempting.

Two cards to rule them all

Longtime readers of the blog know I’m extremely stingy when it comes to annual fees. I do pay them, but expect something upfront. That’s why I have a medley of  cards where I get certificates or points upon renewal. See related post Normally, I don’t have a problem using them to my advantage, though this year has been an outlier for obvious reasons.

There is one exception: Amex Everyday Preferred ($95 fee). I’ve just gotten it via an upgrade from regular Amex Everyday, and there is a 99% chance I will renew it next year. You get no benefits upon renewal, but the ability to earn 4.5 MR points on groceries, 3 points on gas, and 1.5 points on everything else is extremely attractive to me. I’ve really come to appreciate Membership Rewards program, and even though travel is on hold right now, things won’t always be that way. I hope.

You do have to make 30 purchases each month, which is a nuisance, for sure. I just make a point to buy a few $1 Amazon gift cards each time I’m shopping through that website. It takes just a minute of my time to reload the balance, so it’s not a huge deal. Obviously, I wish I didn’t have to worry about it, but we can’t have everything now, can we?

It’s odd that Amex has pretty much stopped promoting this card. In fact, you won’t even find it listed in affiliate channels. But I think it’s one of the best, if not the best, product for middle-class families who are relatively well versed in miles and points. The bonus offer on this card varies, so I recommend you check incognito mode if you want to apply.

I should note that if I lived in a large city, I would seriously look at Amex Gold instead.  See related post Even though the fee is $250, you can potentially get it down to $30 if you are diligent enough.

As it stands, it’s not that easy for me to utilize GrubHub credits and other obscure benefits. YMMV The sign-up offer through my referral link is 40k points compared to 35k via affiliate channels if you choose to apply. So for now, I’m hanging onto my Amex Everyday Preferred, but may eventually swap it for Amex Gold.

What about the second card I feel is absolutely indespensible to my travel strategy? That would be Chase Freedom, no question about it. It has no annual fee, and gives me access to transferrable Ultimate Rewards. Since it earns 5 points per dollar in rotating categories, I can passively accumulate them until a great opportunity presents itself.

I value United miles above any other airline currency, as they saved my butt a few months ago when I had to get my parents out of US pronto. I still have PTSD from checking to see if their Lufthansa flight actually took off from Frankfurt at 10 AM, when EU was planning to seal the border at noon the same day. But I digress…

Anyway, for me, Amex Everyday Preferred+Chase Freedom is the combo to beat. If I could only have two cards in my wallet for the rest of my life, that’s what I would pick. More precisely, I would want access to both Membership Rewards as well as Ultimate Rewards programs at the lowest possible cost.

If like me, you are a person of limited means, I recommend you become ruthless when it comes to annual fees. Those can suck the “free” out of free travel without you even noticing it. Plus, as you can see, sometimes you can actually make money on an upgrade to a premium card.

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Opinions expressed here are author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.