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My Interview with Stephanie, a Mom Trying to Align Miles and Points with School Schedule

Today I would like to introduce my reader Stephanie. She has a typical middle-class family of four, with both kids in school. So, I’m certain that many of you will be able to relate to her situation. Not too long ago, she was kind enough to share her experience of booking award seats to Hawaii via Korean Skypass. Extremely helpful!

So I reached out to Stephanie and asked  if she would be willing to share her musings on this hobby, family and traveling during dreadful peak season. I’m sure you’ll enjoy the interview just like I did.

Here we go:

1) What motivated you to research miles and points hobby?  

Around June 2015, I had received an offer from Hyatt to visit their Hyatt Residence in Kaanapali for 5 nights (super great price for a 2 bedroom/ 2 bath Ocean View Condo) so I booked it for the summer of 2016, but we would have to sit in a timeshare presentation.  We wanted to spend an extra 2 nights at the Hyatt Regency next door, but it was $400+ per night just for a standard no-view room for the 4 of us (ouch!).

I researched points and miles and came across Million Mile Secrets and The Points Guy as I was trying to find 2 free nights for the Hyatt Regency and maybe some points for flights.  I applied for the Chase Hyatt Visa Signature  and got my 2 free nights at Hyatt Regency Maui. We were upgraded to a deluxe ocean view room, resort fees were waived and valet parking was given to us at the same rate as self-parking because of my new Platinum status via credit card. Score!

I also applied for the Chase British Airways Visa since Avios program is supposed to be the best deal to Hawaii from LAX (25,000 miles roundtrip). I am yet to use this sign-up bonus as American Airlines (BA partner) usually has terrible award availability for when we need to travel. But this is the trip that started my obsession with points and miles.

2) What are the biggest challenges you face  trying to navigate miles and points hobby?

Meeting the spend requirements on new cards since I won’t manufacture spend.  Also, finding a balance between collecting, saving, and spending points. I’m a saver so it always makes me nervous to spend our points, but that means I just need to strategize my spending with my existing cards (I have the Chase Freedom, Chase Sapphire Preferred, and Chase Sapphire Reserve).

Also, since we have school aged children, this means we can only travel during peak season (Spring Break, Summer, and Winter Break).  This is not ideal for a family on a tight budget, but I came up with a travel bucket list that is prioritized by location with the season and year.  I’ll make adjustments if I find a great deal or need more time to collect the right points.

3) What’s your favorite trip that was made possible solely due to miles and points?

We have 2 trips scheduled. The first one: 5 nights in Monterey/San Francisco (road trip; using 2 free Fairmont Certificates w/suite upgrade, 1 free night certificate with Hyatt Visa annual renewal, and 2 nights with points & cash for Embassy Suites).

Also: 7 nights in Washington DC (used 50,000 AA miles for 4 one-ways and paid $700 for return flights, and used 42,000 Hyatt points from Chase UR program  transfer, plus $600 cash).  Mind you, these 2 trips are during the High Peak Travel Season, but with a lot of research, planning, and ability to book 9 – 10 months in advance, we are hoping to have 2 wonderful vacations.  

4) How often do you think about miles and points?

Haha…I think about miles and points way too often.  I’m a little obsessed with them at the moment, but I’m hoping I’ll get the hang of it and have a nicely diversified portfolio of points and miles by next year.

5) What is the craziest thing you’ve ever done  to earn miles or points?

Since I don’t have a Hilton card, I’m racking up Hilton points by taking surveys on e-rewards and I cash them out when I reach $100 for 7,000 Hilton points.  I also take Points for Surveys to collect JetBlue currency since their points never expire and you can family pool them.

6) How does your family feel about this hobby?

My husband has been such a good sport, especially since I’ll get him a new card and tell him to spend on it until I tell him to stop (meaning we met the requirement).  He only asked me to never again  sign up for a timeshare presentation.

It was too stressful for him (the Hyatt Residence Kaanapali), but I did get 10,000 Hyatt Points out of it.  My in-laws want me to help them strategize credit card points with their low spending for a NYC trip, so I’m working on that right now.

7) Do you ever wish you never found out about miles and points? Why/why not?

I wish I knew about miles and points years ago, but since I’m new to it, I’m not going to waste any more time.  I rarely traveled as a kid, so seeing new destinations and visiting landmarks with my family is truly priceless.  Also, my children are at the perfect age to travel, so it’s really enjoyable for all of us.

8)  If you could give one piece of advice to someone who is just starting out, what would it be?  

Have an idea of where you would like to travel and do some research (price out flights and hotels) – I love TripAdvisor, Kayak, and Hotel Hustle.  Then only apply for cards where you can meet the minimum spending requirements and pay off the balances (don’t get into debt).

Also, track all your points on AwardWallet and your credit card applications on a spreadsheet.  Lastly, if you need a second opinion, ask for help. I took Leana’s advice, went into a Chase  branch, and was approved for the Chase Sapphire Reserve despite having more than 5 cards within the last 24 months.  


Thank you, Stephanie, for sharing your story! 

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Author: Leana

Leana is the owner and founder of Miles For Family. She enjoys beach vacations and visiting her family in Europe. Originally from Belarus, Leana resides in central Florida with her husband and two children.

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5 thoughts on “My Interview with Stephanie, a Mom Trying to Align Miles and Points with School Schedule

  1. Stephanie, I can’t believe you have the patience for e-rewards and actually accumulate enough points to use on hotel stays! Those drive me crazy.

  2. I was wondering how the e-rewards surveys work for you. I’ve tried taking a few through the IHG survey rewards program. I start the survey, spend a few minutes on it, and then it says they have enough participants in that survey. I guess they aren’t looking for the opinions of a 30-something WAHM. I’ve never been able to get approved to take enough to amount to anything.

  3. MilesForFamily, I only do surveys when I have time as I work and have the family to care for. It usually takes me 3 months to cash out for 7,000 Hilton points. We don’t usually stay at Hiltons, but if I can find a cash + points stay at an Embassy Suites every year or so, then it’s worth it. Just wanted to thank you Leanna for all of your help. You should’ve seen me yesterday, searching for airfare to Europe — it’s a dream of mine to take the family one day, and because now I have points and know which ones to collect, I think we can actually afford to go in a few years.

    • @Stephanie I’m more than happy to help so please, reach out anytime. I do think you can pull off a trip to Europe, it’s just a matter of collecting the right currency. Your CSR bonus can go a long way, plus, you can always use points on paid flights. Feel free to email me if you ever need any help with planning the trip.

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