The Game Was Already Over Before They Got Here.

On April 1, I sat down at my kitchen table and earned over half of my points for the entire competition.

No pesky category bonuses or rifling through a Pokémon binder full of credit cards. I just booked a hotel on the right day of the month, with the right card, through the right travel portal. Exactly one month later, I slipped out on a furtive mission to my local BBQ pit and returned with a prepaid gift card. By the time my guests arrived, my score was already decided, and I’d earned 98.8% of my points for the competition. 

In fact, my in-person spend while Brendan and Erin were in Bloomington amounted to just $6.39 out of a $500 budget.  

The Rove Maneuver 

The Bilt Palladium Card is my daily driver in 2026, and I nearly followed a one-card strategy for the entire challenge with a single interruption by the American Express Platinum Card®. Two cards, two mirror finishes, and some serious “plunk factor.”  

Candidly, my biggest priority during the planning process was to spend as much as I could on the hotel, as little as possible on activities, and max out the rest with dining spend. Double or triple stacking on hotel stays is one of the easiest ways to rack up a ton of points at once.

The rules of the challenge incentivized spending as much of the budget as possible at the highest multiple I could find (without going over the $500 budget, of course).  

The Graduate by Hilton Bloomington was always going to be my hotel pick. The decor is maximalist varsity kitsch, with every hallway featuring a reference to something Hoosier (most prominently, a recurring motif of Coach Bobby Knight throwing chairs).  

It was a foregone conclusion that I would book the room during Bilt’s Rent Day promo (in which base card earnings are doubled on the first of the month up to 1,000 bonus Bilt Points). But even with that in mind, I priced the same room three different ways: 

• Booking direct through Hilton: would have earned me 4x Bilt points plus 18 Hilton points per dollar as a Gold elite member. Which sounds nice until you remember that Hilton Honors points are valued at a measly $0.005 each.  

• Bilt's travel portal: unremarkable, earning a flat 6x for the night. 

• Rove: was running a 23x Miles Boost promotion and I paid with my Bilt Palladium Card, earning another 4x in Bilt points as a Rent Day stack. While some Rove bookings are loyalty eligible and allow you to triple stack shopping portal, credit card, and hotel points earnings, this one unfortunately was not. That didn’t stop us appending a Hilton number to the reservation, however. We didn’t earn any extra points, but the hotel did honor a $30 dining credit for Gold members.  

At $0.015 per Rove Mile times 23x, I was getting back $0.345 per dollar from the portal alone, roughly seven times what Hilton Honors would have given me on the same stay. The room cost me $277.53 on April 1. That single transaction generated 5,500 Rove Miles plus 1,110 Bilt points for 6,610 points total ($106.92 in weighted value), about 62% of my final total. 

Buying Dinner the Night Before 

Even points professionals – those of us who do this for a living – occasionally stand at a register with three credit cards fanned out like we're about to perform a card trick at a child's birthday party, trying to remember whether this particular sandwich stand codes as dining or, bafflingly, automotive repair (a true story for another day).  

I didn’t want to fumble the competition by missing a category bonus or going over budget, so on May 1, I found myself making another Rent Day purchase at a local restaurant, Smokeworks. I make no claim that they're the best barbecue around, but it is the only Bilt Neighborhood Dining restaurant in town, which has a quality all its own. Specifically, an extra 3x points on top of my usual earnings, which means a total of 7x Bilt points earned on Rent Day.

What the app didn't tell me – but local knowledge did –  was that Smokeworks belongs to Finney Hospitality, a restaurant consortium which operates four total restaurants and, bizarrely, a car wash. That one gift card could be freely redeemed group-wide at any of these businesses.  

We redeemed $125.95 on the gift card during the weekend itself, locking in 882 Bilt points at 7x. The same dollars at the table on Sunday would have earned just 378 points.  

With my plan mostly already deployed, it was time to pick up the stars of the show.  

Day 1: Varsity Colors 

I drove up to Indianapolis alone on Sunday morning, picked up Brendan and Erin at the airport, and took them straight to The Elm for brunch. 

The Elm is the only Resy restaurant in Bloomington, which means that I eat there quarterly whether I like it or not.  The Platinum Card®’s Resy credit* was, let's say, a feather in my cap. We ate. We talked. Brendan, ever the professional, photographed our food. I paid the $106.39 bill with my Amex, knowing that my card’s credit would reimburse $100 of it, I would still earn 107 Amex points on the full charge, and we'd reduced the out-of-pocket cost of one of the best farm-to-table meals in town to $6.39. 

(*Get up to $100 in statement credits each quarter when you use the Platinum Card® to make eligible purchases with Resy, including dining purchases at U.S. Resy restaurants. Enrollment required.) 

Since Bloomington was the final stop in the entire Points Pursuit series, I made the call to keep the schedule light. After brunch, we dropped in on an Indiana University softball game. The Hoosiers were closing out their regular season, and it was their final game before exam week. I wanted Brendan and Erin to see Bloomington in its varsity colors. The bleachers were packed. The sun was out. Indiana won. It was the kind of unfussy, free-or-cheap Sunday afternoon that defines a college town. 

Plus, we had important work to attend to after that. It's a Sunday tradition in my family to cook Vietnamese pho (my wife is from Hanoi), so we dropped by my house for a quick cooking demo. We smoked spices, charred onions, and began simmering a rich beef broth for our breakfast the following morning. By mid-afternoon, the pot went on the stove, where it would simmer until Monday morning.  

After a quick rest at the Graduate, we turned out for a progressive dinner across Bloomington’s courthouse square. Appetizers at The Tap. BBQ at Smokeworks. Tacos at Social Cantina. A nightcap at Yogi's. All four restaurants were walkable within a few blocks of each other and the hotel. All four were paid for from the same gift card, and the deployment was so smooth it felt anticlimactic.  

Day 2: No Cereal Allowed 

Pho for breakfast is one of those Vietnamese traditions that doesn't make any sense until you've had it, at which point you wonder why you've spent your entire life eating cereal.

We assembled our bowls with rice noodles, brisket, herbs, bean sprouts, lime, and fish sauce. It was a rich mélange made all the more savory by the fact that I’d bought the ingredients the week prior with a 12x stack through the Rakuten shopping portal. All of this was served alongside loaves of sourdough bread bought through the AAdvantage shopping portal. 

After breakfast, we had a leisurely drive back to the airport. Total in-person spend across the entire 24-hour window: $6.39.  

Total points earned during the 24 hours: about 107 Amex MR. 

I played the competition the month before, making the challenge one of calendar – rather than category – management: 

Total points earned: ~9,841. Weighted value: $171.78. Blended return: 34.4% on $499.84. 

Watch the video here.