The 10 worst things I ever bought

This post comes from Len Penzo at partner blog Len Penzo dot Com.

Last year, I looked back with fond memories at the 10 best things I ever bought. At the time, I had intended to immediately publish a follow-up article up on the 10 worst things I ever bought, but I got a bit side-tracked. After a lot of thought, I'm happy to say I finally finished.

Interestingly, this list was a lot more difficult to compile. Unlike my 10 best list, I really had to dig deep and think hard about the purchases that gave me the worst cases of buyer's remorse.

So without further ado, here's my list -- in no particular order, of course. How does it compare with yours?

1. My first house

Purchase date: 1990
Purchase orice: $114,000
Why it's in my bottom 10: OK, I said these items were in no particular order, but this one takes the cake. I bought my first house at the top of the market. As a result, I spent the next seven years owing more than it was worth, which meant I couldn't sell it unless I wanted to shell out about $20,000 to make my lender whole. So I chose to ride out the downturn, which is a reasonable strategy for most people. Unfortunately for me, this house was in a less-than-desirable neighborhood, just 100 yards from a very busy -- and extremely loud -- rail line that carried freight and commuter trains 24/7. I know.

2. Our ottoman

Purchase date: 2000
Purchase price: $400
Why it's in my bottom 10: When we finally replaced our hand-me-down sectional with a brand-new leather sofa and love seat set, the Honeybee insisted on getting the optional wheeled ottoman too. "It'll never get used," I said. She insisted otherwise. Of course, she was right, but only because the kids used to pretend it was a car and "drive" it around the house. Now that the kids are older, the ottoman just sits in the corner, collecting dust.

3. A double stack guitar amplifier

Purchase date: 1993
Purchase price: $995

Why it's in my bottom 10: When I was in my 20s, I had big dreams: I was going to be a rock 'n' roll star! Of course, that meant playing the part, so I grew my hair out and bought a double stack guitar amplifier. Talk about overkill. I could have played Dodger Stadium with that thing if I wanted to. The trouble is, most of the time we were playing small bars and other venues that required more compact equipment with half the power -- or less. (Post continues below video.)

4. A vacation in the Bahamas

Purchase date: 1990
Purchase price: $1,000 (approximate)

Why it's in my bottom 10: My girlfriend at the time decided to surprise me with a ridiculously priced travel package "deal" to the Bahamas. For $199 we got a romantic "cruise" to our destination in Freeport, and seven days and six nights of lodging at a local "resort." Of course, the airfare, food, and other expenses weren't included, but we didn't care because we got the deal of a lifetime! Or so we thought. The cruise was on a rickety old glorified fishing boat and the resort was a run-down old apartment in the worst part of Freeport, miles from the beach. And it rained incessantly. Without a doubt, it was my worst vacation ever.

5. My Sony 400 CD player

Purchase date: 2001
Purchase price: $295

Why it's in my bottom 10: Remember those things? The first time I laid eyes on Sony's CDP-CX400, I thought I had died and gone to heaven. Yes, the machines were humongous and bulky -- after all, they tipped the scales at 9 pounds. True, they also had a clumsy programming interface. But this baby allowed me to store, play and shuffle 400 (400!) music discs, which meant I could finally dump my space-wasting CD racks in the trash. Even so, my love affair with the CDP-CX400 ended less than a year after I bought it. That's because Apple unleashed a brand-new invention called the iPod, which essentially rendered the CDP-CX400 obsolete.

6. My backyard irrigation system

Purchase date: 1998
Purchase price: $1,500 (approximate)

Why it's in my bottom 10: When you're evaluating multiple contractor bids for anything, the lowest price is not necessarily the best deal, especially if the lowest price is significantly less than the other offers. To this day I'm occasionally reminded exactly why I was able to get such a "great" deal on my irrigation system. The answer is revealed every time a sprinkler pipe bursts, thanks to the shoddy material the contractor used to cut corners.

7. Movie rental: "The Good German"

Purchase date: 2009
Purchase price: $1 (rental price)

Why it's in my bottom 10: Laugh all you want. This movie was so bad that if I had snuck into the theater to see it I'd still demand my money back. Anyway, if you're a glutton for punishment, you can check out my official movie review here.

8. My Los Angeles Kings Alexei Zhitnik hockey jersey

Purchase date: 1994
Purchase price: $120

Why it's in my bottom 10: Back in 1994, it was time to buy myself a new Los Angeles Kings hockey jersey. Of course, being the contrarian doofus that I am, I decided it would be cooler to have promising young defenseman Alexei Zhitnik's name and number sewed onto the back of it. After all, everybody had a Kings jersey with the great Wayne Gretzky's name and number. Dumb move. Less than a year later, the Kings traded Zhitnik to the Buffalo Sabres for a Zamboni machine and a couple of old hockey pucks. I still wear the jersey on occasion, but I'll always regret not putting Gretzky's name on the back when I had the chance.

9. My whirlpool tub

Purchase date: 1997
Purchase price: $600

Why it's in my bottom 10: When we bought our current home, the builder asked us if we wanted to "upgrade" our master bath with a whirlpool tub. Being young and naive, I jumped at the chance. Big mistake. Within a few months of moving into our new home, it was painfully obvious that the disadvantages of whirlpool tubs far outweigh their advantages. So much so that we never use ours anymore. Trust me: Whirlpool tubs are for suckers. 

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10. A very disappointing dinner in Maui

Purchase date: 2011
Purchase price: $150 (tip included)

Why it's in my bottom 10: The Honeybee and I were vacationing in Wailea, Hawaii, and happened upon a fine dining place that was showcasing photos of the owner posing with rocker Steven Tyler in the restaurant's dining room. Cool! Naturally, we figured if Steven Tyler was willing to pose for pictures with the owner, the food there must be fabulous, right? Wrong. You can bet that's the last time I ever go to any restaurant with photos of Steven Tyler at the front door.

More from Len Penzo dot Com and MSN Money:

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• 21 reasons why corner lots are for suckers
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