Off-the-wall things my family has done to earn more points and miles

Quick: What's the most off-the-wall thing you've ever done to earn extra points and miles?

If your friends and family don't really participate in this hobby, they may consider everything you do "weird." I asked my wife what she thinks the weirdest thing I've done for points and miles is, and her response was akin to "everything."

Barring the mindset that "applying for lots of credit cards is weird," let's look at some of the more unique things my family has done to earn lots of points and miles.

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For starters, I don't consider these 2 things to be strange

Before we continue, I want to mention that some things my friends and relatives may consider strange really aren't that odd -- at least not in my view.

I don't find having more than 20 credit cards to be that strange. In fact, maybe I should write an article explaining why my wife and I each have 20-plus credit cards and how we get value from all of them -- beyond just the sign-up bonus.

And when I go out to eat with friends or relatives, you can be sure that I will volunteer to pay the bill with my credit card while everyone else just gives me their money. I'll use my best credit card for dining to pay for the meals of people who were planning to pay cash anyway, earning bonus points that don't cost me anything -- a real treat.

So, no, I don't consider these things weird. I consider them pretty normal.

The strangest things my family has done to earn more points and miles

You may be thinking, "If those aren't weird for you, what is weird?" Here are some of the more off-the-wall things my family has done to earn extra points and miles.

Split purchases into separate transactions

Last year, there was a promotion for Hyatt credit cardmembers to earn bonus points after making numerous transactions in a month. The best value from this promotion obviously came from making lots of small transactions with low price points. Each transaction only needed to be $1 or above to qualify.

While at the supermarket, I paid for each item in my shopping cart individually. Fifty-plus items, each priced over $1 -- and I earned 5,000 bonus World of Hyatt points. Based on TPG’s valuations, 5,000 World of Hyatt points are worth $85.

Yes, you could try this at the self-checkout. However, I felt it would look really suspicious, so I went to a cashier. To be clear, I only did this when there was no line and the cashier didn't mind. I wouldn't subject others to waiting extra time unnecessarily.

Similarly, my wife and I used a less eccentric version of this same concept just this month. I received an offer to "tap to pay" three times on my Chase Freedom Flex. If each transaction totaled $1.75 or higher, I could get $5 cash back. My wife received a similar offer on her Marriott Bonvoy Boundless Credit Card of 500 bonus Marriott Bonvoy points after three "tap to pay" transactions of $1.75 or more. According to TPG’s valuations, those points are worth a little over $4.

During two separate visits to a nearby 7-Eleven, we bought chips, a Coke and some candy, with each item as a separate transaction. Of course, we tapped our cards to pay and met the requirements for the three transactions each, netting those bonus points on things we were going to buy anyway -- we just approached the payment differently.

Labeling my wife's credit cards

Admittedly, my wife is not well versed in the points and miles hobby. She applies for credit cards and closes them based on what I recommend to her.

Keeping track of the many credit cards she has, and their bonus-earning categories, is a bit beyond her knowledge of points and miles. Instead of overwhelming her, I've made things simpler over the years. She carries just two "all the time" cards in her wallet: the Chase Sapphire Reserve for its earnings at restaurants and on travel, and the World of Hyatt Credit Card as we work toward the free night award that comes from spending $15,000 on the card each calendar year.

I've labeled these two cards to help her remember which purchases are best for which card. There may also be a third card in her wallet at any given time: the card for which she is working on a new sign-up bonus. She will recognize that card by it not being one of the regular cards in her wallet and can use it for any purchase.

This system helps us maximize points and miles on each purchase without making it complicated, without her worrying about messing up and without me needing to remind her which card to use for each purchase. It might seem strange, but these labels can give us 1 or 2 extra points on every purchase over the course of the year.

Paying with my card and keeping the cash from strangers

Have you ever had that feeling of "I can't believe they're paying cash! They could be earning so many points!" when you see strangers handing over real money to a cashier? I have. One time, I decided to do something about it.

I had just opened a new credit card with a significant spending requirement to earn the sign-up bonus. I was also at the Apple Store to buy an Apple Watch as a Christmas gift for my wife.

The family in line in front of me was buying multiple iPhones and a laptop and planning to pay cash. I saw a golden opportunity: I took their cash and paid for everything on my credit card. On the way home, I stopped at the bank to deposit the cash and smiled at the more than $4,000 I had just put toward earning my card's sign-up bonus.

The family definitely thought I was strange. I showed them my ID and promised this was legitimate -- I just wanted to earn the credit card points, I explained. In the end, this definitely worked in my favor. I'm always on the lookout for another opportunity to do this.

Earning a sign-up bonus from funeral expenses

Everyone dies. And funerals can be expensive. If we strip the emotion out of it, remember that one of our most basic tips is to put all of your spending on your new credit card to help earn the sign-up bonus. And if you have a large purchase or significant spending coming up soon, that can be a great time to open a new credit card, in order to use the spending toward the welcome offer.

When my grandmother died a few years ago, this is exactly what my mom did. She put the funeral expenses on a new credit card and earned a bunch of frequent flyer miles in the process. While it didn't bring Grandma back or cure our sadness, it was a silver lining for my grieving mother.

Bottom line

When it comes to earning points and miles in my family, we've done some things that are ... let's call them "unique." However, they all fall under the guiding principles that you should always be working on a sign-up bonus, or, if you aren't, using the best credit card available for the purchase at hand.

A little creative thinking can help you turn an errand — such as grocery shopping — into a windfall of bonus points. It all depends on how you pay for the transaction and what other opportunities you can find for earning more points without increasing your own out-of-pocket expenses.

Next time you see people paying cash for expensive items, I bet you'll think about this post.