MMMT: The 5 Deals I Missed Out On Since Joining the Hobby

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The 5 Deals I Missed Out On Since Joining the Hobby

Monday Morning Miles Talk is a regular series that has some smaller, more quirky ideas to kick off the work week.  These are essentially random ideas that I wanted to share with you.  Here are the previous entries.

If you would like to read some of the other articles in the series you can click HERE.

The 5 Deals I Missed Out On Since Joining the Hobby

With it being a new year and all I find myself reflecting some.  I started taking a look back at how I would handle applications if I was just starting out now with my Clean Slate Series.  And while thinking about that I started thinking about other things I wish I would have done differently.  As they say, hind sight is 20/20!

I find myself regretting things I didn’t do more often than regretting the things I did do.  So get ready for some big time regrets on missing out!

The List

These are in no particular order but they are my top 5 regrets/deals I missed out on:

Cashing out my 50,000 Chase Sapphire Preferred Sign Up Bonus

I first got into this realm not to travel so much but as a way to make some extra money.  I had been told about a card that could make me a quick and easy $500.  At the time I thought I was getting a great deal…$500 for spending $3000 on a credit card.  If I had only known at the time how much value I could have gotten out of it!

The silver lining is it did lead me down the travel “hobby” wormhole so I am grateful for that.  It all worked out in the end!

Pain Factor – 4/5

CLICK HERE to get more details and learn how to apply for this card and other travel rewards credit cards!

The 5 Deals I Missed Out On Since Joining the Hobby

Not Hitting the Target RedBird Harder

The Target RedBird was probably the easiest way to increase spend since the US Mint Coin trick.  It only lasted a few months but it was extremely easy.  Many people got their hands on multiple RedBird accounts to increase their bandwidth.  I foolishly stuck with one for myself and added my wife a little later on down the road.  Some months I didn’t even max both of them out…the horror!!!

I was newer into the increased spending realm at this time and I was worried about upsetting American Express for some reason.  My naivety and paranoia cost me tens of thousands of points.  This was a fee free way to rack up a ton of miles and points.  There may never be anything quite as easy again.

Pain Factor – 4.5/5

Not Signing up For the Chase Sapphire Reserve Day 1

When the CSR was first released their was an error in Chase’s system, whether intended or not, that let people with over 5 applications in the last 24 months get approved.  I read the reports but I really thought that Chase would retroactively deny the cards after they were approved.

I had also recently signed up for 2 American Express Platinum 100K offers. One for myself and one for my wife.  Having just spent $900 on annual fees I wasn’t looking forward to adding another $450 to the pot.

Knowing what I do now, and with how hard it is to get Ultimate Reward sign up bonuses, I should have jumped at the chance of getting the card.  I held out hope that myself or my wife would get a targeted offer, when those were still working to bypass 5/24, but it never came.  I missed out on a golden opportunity to get 100,000 UR points.

  Pain Factor – 5/5

CLICK HERE to get more details and learn how to apply for this card and other travel rewards credit cards!

The 5 Deals I Missed Out On Since Joining the Hobby

Missing Out on the Citibank Gold Checking Account Sign Ups and Funding

I actually did try to get this one but I had waited a little to long to pull the trigger.  If I am being honest, I despise Citibank and their customer service department.  That is why I dragged my feet applying for this.  I had read the horror stories of fighting to get the Aadvantage Miles or ThankYou points and I wasn’t looking forward to fighting to get the bonus.  The chance to fund the account with $20-50,000 etc. is what finally drew me in.

I was having issues with the online application and had to call in to finish the application.  The phone rep told me, point blank, that if I hadn’t been targeted for the offer they were starting to deny the bonuses.  I decided it wasn’t worth the hassle or the fight and canceled my application.  If I had only gotten around to it a few months earlier I could have been sitting on 75-100k in miles or points.

Pain Factor – 2.5/5

Not Getting the Ritz Carlton 140,000 Point Offer

There was a short lived AMAZING offer for the Ritz Carlton card from Chase for a 140,000 points.  Normally the Ritz Carlton card offers 2 or 3 free nights in a category 1-4 hotel.  But at the end of 2014 they offered 140,000 Marriott points instead.

That 140,000 points would have gotten me a big chunk of the way to a nights and flights package from Marriott.  Those packages were still working towards the companion pass back then.

I had recently applied for a couple of higher annual fee cards and didn’t want to add another one at the time.  I foolishly thought the offer would return at some point in the future. My cheapness got in the way of two of the deals on this list…I won’t let that happen again!

Pain Factor – 3/5


There are some painful memories in there that probably cost me close to a half a million miles and points.  If only I could invent a time machine!

Let me know what your biggest regrets are in the comments section.  Did any of yours match up to mine?


Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

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  1. I am so grateful for these posts… I smile, and think how I have probably outdone all of you with so many absolute bonehead moves over 30 years before I discovered the blogs and new info.
    My worst one: Was offered a complimentary matching ticket by a AA agent for my son when flying to Hong Kong and Tokyo business class (I swear they did that back then) and dumbass me said… “I will think about it.”
    Genius here was convinced there was a catch. Of course, the offer was no longer there the next day. It was truly an amazing program.
    Shame AA miles are worthless now.

  2. I’ve only been in the game less than 2 years, but mine are:
    1) wasting 2 of my 5/24 slots before I knew what I was doing (and wasting another on a Chase Freedom). Pain factor 5/5
    2) screwing up my CIP app, thinking it was paper app through CRM, now with Chase shutdown stories, risk is too great to try again. Pain factor 3/5
    3) paying for global entry on my own before convincing myself that paying $350/$450 for annual fee might make sense. Pain factor 2/5
    4) wasting 80k United points on an international economy ticket, when I should have used MR pay with points with 50% rebate. Pain factor 2/5
    5) missing out on ML+ (though I tried) Pain factor 2/5

    • Those are some good ones – thanks for sharing. I also missed out on the ML+ – I was initially approved and then retroactively denied a few days later. Luckily my wife was able to get one though!

  3. 1) Cancelling our United card because I didn’t understand the value of the increased award availability;
    2) Getting a Capital One card when I was under 5/24 because I hadn’t even heard of 5/24 and cash back seemed cool and easy to use.
    3) Not grabbing a Fairmont card in the days before it’s demise. Those are good value and they let my spouse turn his into a CSP and then another Freedom so that alone would have been worth it.
    4) Booking a ticket to Peru through the Chase portal.
    5) Not having one of us get an Ink card with our last 5/24 spot. My spouse got a SW card but we really don’t fly SW. Ugh.
    The brutality.

    • Those are some good ones. Good point about the Fairmont transferring over to another Freedom card…super valuable.

      On the Peru one would booking it with points via United etc. saved you a ton of points?

      • I could have booked on AA for less I just got so frustrated with them and I didn’t understand how to deal with AA redemptions at that point. Now I still have tons of AA miles and no great use for them. Sigh. But the United Card is honestly the one that hurts the worst. I can earn more points. I can’t open up award availability that cardholders have.

        • That is true – United doesn’t really work for me at my home airport but that is a very valuable perk.

          AA – I feel your pain there…#6 on my list would have been transferring SPG points to AA for the 20k to 30k bonus and then they devalued it a few months later leaving me with a large balance and no availability.

    • I PCd my own Fairmont card to a Freedom Unlimited. My back-up when a non-bonused spend merchant doesn’t accept AMEX (SPG).

  4. My biggest regret was not “buying” lifetime Fairmont Platinum status for $2k about 7 yrs. ago. I could have easily recouped my investment within a year & then free nights/suite upgrades, etc. would have been mine from then on. Like you I was short-sighted and/or just the deal seemed too good to actually be true. Still to this day, though, I have never given LivingSocial (who offered the deal) that much $!

    Fairmont has my absolute favorite loyalty program & although it’s being merged into Accor Hotels in July (& the terms changed), still they are offering me a complete set of double e-certificates come July because of the merger! They are the best!

    I don’t know if Accor will continue to recognize lifetime Platinum status for those folks who did that deal, but I would’ve more than realized my money’s worth in 7 years of use anyway. I think the overall loss of the existing Fairmont Presidents Club program, though out of my control, is probably my biggest regret!

    • That would have been a good one for sure – especially for your favorite program. I hope Accor does something for anyone who bought in or earned it.

      • I have been earning Platinum status annually the hard way! Today Fairmont emailed transition plans:

        “Your Fairmont President’s Club membership will continue until July 1, 2018. On July 2, 2018 you will receive a Platinum membership with Le Club AccorHotels, the most elite tier in the program.

        As a gesture of our gratitude for your loyalty through this transition, you will be eligible to receive as a bonus another full set of Fairmont President’s Club e-certificates in July. This will be in addition to the e-certificates you receive in March.* All you need to do is have two qualifying stays with Fairmont, Raffles or Swissôtel between January 1 and July 1, 2018.”

        Fair enough…done, as I already have Fairmont stays booked anyway!

      • I am (was?) one of the Lifetime Platinum Fairmont members. I have not received a transition email, although my wife did as a Premier member. Has anyone heard about the transition for Lifetime Platinum Fairmont members?

  5. Interesting you have a place where you show which cards you are currently signing up for or have recently.. thanks


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