Man, do I feel your pain. Well, I’m only 5 years into the King County experience but sheesh…
Easily my motorcycles. It’s not that they break down or anything like that. It’s just that I always see something new, or want some more chrome, or something childish. Especially when it comes to my Harley. A good motorcycle is more like a mistress than a mode of transportation.
Yes, my thinking exactly. The concept of a money pit implies not just spending a lot of money on something but it also not living up to expectations, e.g. not producing sufficient return.
If you willingly spend money on a hobby you enjoy, that’s not a money pit…unless possibly if you thought the hobby was going to be much cheaper initially and now are too invested.
The OP defines money pit as “an activity that has no chance of returning on financial investment”…but then gives some examples where no investment was made and no return expected 
I don’t think anyone here is wealthy enough for that level of money-pit-ness! 
Back in 1986 I purchased a domestic hot water heating system for my home. I calculated the payback period to be about 15 years. After 5 years the holding tank failed and set my payback period back another 7 years. The breakeven point became 2008. The system was mothballed from 2003 to 2007 and then relocated to my current home. The cost of installing it here pushed the payback period along another 3 years. At this point, in 2016, the thing has finally paid for itself, barely. In fairness, when operational it’s great. But after 30 years I consider this my money pit.
I’ve never gotten why people begrudge bike’s their running cost - it still isn’t much compared to cars.
As for my money pit - I finally tracked down a 1975 Honda CB500T. It was only $900 and it’s running fine, but I’ve set aside another grand to make it nicer, after which it will be worth maybe a grand. 
Cocaine. Definitely not getting my return on that financial investment.
Sounds like you’re the money pit!
(I am one, now that I think of it!)
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It would be tennis for me. I’ve spent thousands over the years on equipment, court fees, stringing, and travel.
A gelding named Cody and a mare named Lacey.
Perfume. Yes, I earn some money blogging, reviewing, and otherwise taking advantage of my expertise on the subject, but I spend much more than I earn acquiring vintage bits of this or that or some particularly fine example of an early 1900s art glass bottle, etc. etc.
Gadgets for me. If it has a purpose and I don’t have one, I want one. Even If I have no conceivable use for it. A couple days ago I was looking online for a high-end scientific ph meter. For no reason at all, and no idea what I would use it on, let alone a compelling reason why I needed one different than the cheap one I have and don’t use. Just got a random bug that I felt like I should have one
Fortunately good sense prevailed this time and I didn’t get one, but the battle is not always successful.
I tend to put too much money into old trucks, engines transmissions, I go through them. I get tired of seeing them parked and not being used so I sell them at a huge loss. A few years go by and I want another old truck.
Making primitve bows and arrows for the past 20 years has sucked way too much money out of me. The wood is very expensive as I cannot harvest my own around here.
A few months ago a guy gave me an old 1933 bandsaw, I spent a couple hundred on that probably worth $100.00 at the most.
Definitely travel and vacations for me.
Other than visiting family and the occasional day or weekend trip, I never really traveled to a vacation destination until 2007 when I took the family to Walt Disney World. Since then, we’ve gone on a week-long (or longer) vacation trip at least once (and sometimes twice) every year since. We’ve gone back to WDW numerous times (which we really enjoy), have taken several cruises, and went to Europe a couple of years ago. This summer, we’re finally going to Hawaii. 
What changed? In 2006, my father passed away unexpectedly, as did both of my wife’s parents. My wife’s father never did anything fun his whole life. Instead, he paid off his house early and saved well for retirement. When he finally retired, his wife promptly developed Alzheimer’s, so instead of traveling or enjoying life, he blew his entire retirement savings at the casino…right before dying of pancreatic cancer.
I decided then that saving for retirement is all well and good, but that I also wanted to be able to enjoy life while my wife and I are healthy enough to do so. So instead of just dreaming about going to Paris or Hawaii someday, we’re doing it now.
Also, last year my son and I got certified in scuba diving. Definitely not a cheap hobby, but I decided I wasn’t going to put it off anymore.
One potential money pit that I have probably crossed off my list is getting a private pilot license. I always wanted to learn to fly, but never had the time (or money) to make it happen. However, my uncle recently bought a small plane (a 1974 Piper), and he took me up in it last month and let me take the controls. For some reason, it wasn’t nearly as much fun as I thought it would be. Instead, the whole experience just seemed like a very easy way to get yourself killed. 
I’m living in it. A $30,000 house that has sucked 5 times that out of my life and counting. And it will never be more than it is.
If your kid plays a sport at a high level that’s pretty much it.
This last, for me; and basically, not mind-improving. I have several favourite authors, none of them rateable as mental giants, whose latest I can never resist – including, in hardback.
N/M
Custody battle. The thermonuclear bomb of financial destruction.
I’m curious - is it the house itself or you? My house was $36k and is fine, but I could easily spend as much again fixing stuff that ain’t broke. The kitchen is perfectly fine, but man do I hate that room. And if I fix that, I’ve got to do the bathrooms, and then…