When Yeahs Become Regrets – Part 2

Yesterday, I shared some of the top eight purchases regretted by retirees according to the YouTube channel A Resilient Life. Today, I want to share some of my purchases I regret…even if I didn’t make the purchase.

As I was contemplating this topic yesterday, I did a quick check through my house and thought about past purchases.

What I soon realized is that I have been “saved” from many of these regrets due to my focus on the concepts of “enough” and minimalism.

That said, there are a few worth talking about.

But the real regrets I have are mostly about how I have used my time.

Purchases I Regret, But Don’t Regret

RVs

I bought two Vespa scooters back in 2012.

I almost bought two brand-new Buddy scooters of a similar size, but my frugality won out. Instead, I bought a 200cc and a 175cc Vespa off Craigslist. These were nice scooters. I paid about half of what the two new scooters would have cost me.

Here’s the problem, though.

First, I had no one to ride them with.

Second, I had little time to ride them.

Third, I found out that in my state you are required to have a motorcycle license to ride a scooter over 50cc on the street. They were both street-legal machines, but my credentials were not. That would have required two days of prep, attendance, testing, etc. to achieve.

So what did I do?

I bought a used 50cc Buddy scooter, too.

What the heck?

I basically gave the other two Vespas away after ten years of them just sitting there on battery tenders.

I calculated the cost per ride, and it came out to around $15 per ride. And these were two- to four-mile trips around my neighborhood. Nothing too exciting there. Certainly not the Born to Be Wild dreams I had about tooling around from town to town.

I still have the 50cc scooter, but it will soon be gone, too.

I learned my lesson on recreational vehicles with this purchase.

A Bigger, Nicer House with a View

Oh Lord, the time I have spent scrolling through Zillow listings for a “dream” home.

If I think of it as a hobby, that’s fine. But no, I was serious, particularly in 2017.

I spent Over $20,000 getting my house prepped to sell, and I put offers in on three places.

The first place was a condo/townhouse in town. It had the view. It was affordable. I was steps away from great attractions. But ugh…I couldn’t see having my only home be a condo or townhouse. And the floor plan was wonky. It was basically a two-bedroom with a huge primary en suite that opened to the living room below like a balcony. No privacy.

I backed out in one day.

So I focused on houses.

I found two that I really liked.

The first one would have required another $40,000 to make the deal work, and I didn’t think it was worth it.

The second one I thought for sure I was going to get. My realtor asked me to write a letter to the owners telling them how excited I was about the purchase.

I did.

It didn’t work.

I will never do that again.

Bottom line, I decided to take the extra cash I had built up to “upgrade” from my current home, and Instead, completely paId off the mortgage before the year ended.

It’s Possible I have never made a smarter decision.

A Vacation / Second Home

I came within a whisker of buying a townhouse that had been advertised as having more than 250 additional square feet than the listing actually indicated.

That cost me my earnest money and an attorney fee because the developer was trying to play hardball.

I kept asking for the blueprint with the measurements so we could compare mine with theirs.

The developer refused.

Right before I was released from the contract, the developer asked my attorney if I would be interested in the place for $30,000 less.

My response?

“Oh, and they’ll provide me their measurements of the square footage, too?”

Ha.

About a year later, I was visiting my son and rented an Airbnb in an upscale downtown complex. It was in a very walkable area. It was super nice. And it was quiet. There was no neighbor noise through the walls.

Wow, I thought. Apartment living has come a long way. Maybe I should consider this instead of buying?

And I did.

I now have a great 2-bedroom, 2-bath apartment with about 1,200 square feet in a luxury complex. It has upscale design, an incredible view, a secure parking garage, swimming pool, exercise rooms, lounge, billiards, and it’s right in the heart of the city and very walkable.

Compare that to the 2-bedroom, 2.5-bath townhouse with a limited view, poor walkability, none of the amenities, terrible parking, HOA fees, and property taxes.

The base cost was $385,000 for the townhouse, as my offer was in cash.

My investment of $240,000 completely paid for the apartment rent, utilities, and parking garage space last year, and I am on track to do the same this year.

That’s a Big win.

Side Projects

This is the category where I most often spend money on things I later regret.

Case in point, a friend and I were getting serious about starting a podcast.

What did I do?

I went and bought extremely nice microphones, a top-of-the-line podcast mixer, retractable microphone arms, cables, and the rest of the setup.

Then the 2020 pandemic hit.

The side project was shelved.

The equipment still sits unused on a top shelf in a closet.

I could go on and on, but you get the picture.

Coming Next

In tomorrow’s post, or sometime this week, I will return for Part 3 of this series, in which I will discuss more regrets I have had since becoming FIRE.

This will connect back to the “Top 10 Things I Will Regret Not Doing in the Next 10–20 Years” exercise I introduced yesterday.

Until then, happy shopping!