Avoiding 'Pop Up Jail' and Dealing with Declines

In addition to our regular weekly podcast, we also host an Ask Us Anything Live on YouTube once a month where the Frequent Miler team answers listener questions about points, miles, rewards cards, and whatever else comes to mind. This episode (64) was streamed live on Jan 31, 2024 and can be viewed in full here: Frequent Miler Live: Ask Us Anything   Here are all the questions asked during this episode (with timestamps)

(00:44) - Should Nick upgrade his Aviator card? 

(04:12) - Would you advise to get United Club card and pay the annual fee with 30k points? Is it a good deal? 

(06:03) -Just got my first Amex a BLUE BUSSINESS PLUS. how do I avoid pop up jail when I’m ready to apply to other Amex cards 

(07:27) - Chase and Barclays have declined me due to too many credit checks. How do you work around this? 

(09:38) - What are the best hotel keeper cards currently?

(14:32) - ​What is a reasonable cost to upgrade from economy to business on a transatlantic flight? 

(16:36) - I have the Bonvoy Boundless, planning on getting the Brilliant, and then upgrading the Boundless to the Ritz-Carlton. What is the best timing for upgrading and applying to get all the free night certs? 

(19:34) - Does it make sense to transfer Chase points to Marriott to top up free night certificates? 

(22:06) - Would you hold off on getting American Airlines cards, given your prediction that a devaluation is coming soon? 

(27:18) - This question is for everyone. If you could live anywhere in the U.S., or the world for that matter, based solely on travel hocking opportunities, where would you live? 

(31:58)- What's your prediction on Wells Fargo transfer partners, there was a leak that WF autograph Journey is getting 5x on hotels, 4x on airlines, 3x on travel and dining with $95 annual fee 

(33:19) - Is it worth spending $15K on your Hyatt card through Plastiq to get a free night certificate? 

(34:29) - Will Chase not approve my SouthWest Performance Business card if I didn’t put any post-sign-up-bonus spend on my SouthWest Premier Business card I got a few months ago? 

(35:09) - How do I keep my Delta Platinum status or get to Diamond this year 

(36:30) - ​Has Bilt changed the game with their 150% transfer bonuses regarding the rule of thumb against doing speculative transfers?

(42:30) - What credit card would you recommended to maximize hotel award redemption for a family of five?

(45:59) - With all AMEX Platinums being part of the same family and can only get one sign up bonus for this family, are there any strategies or benefits to getting more than one AMEX Platinums (of any version)?

(48:43) - How is Greg dealing with Detroit Lion loss to the San Francisco 49ers? Which city has best airline and hotel redemption to Vegas?

(53:00)- ​I'd love to hear some hotel tips from things Stephen has learned from his 50 state road trip. I'm planning a month long road trip and would love tips on maximizing value of points