Complete rebuild of the truck braking system. $1500 Only things not replaced were one caliper and the master cylinder.
New used car to replace truck during downtime. $2000 Hit a board on the road $60 tire.
15 yo water heater. $2000 Gas valve control board went out and no replacements - obsolete.
Daughter went to a one week seminar two states away. $1000 but I did mom’s birthday alone in the hotel the night before picking her up so I count that as a plus.
Blew up fireplace control board when a neutral wire opened. $250. Could have been worse as the entire media system was also on that circuit.
Water softener is still on bypass. Truck needs tires.
10,000 for a new roof. Looks a lot like the old roof.
I guess if we’re measuring severity by out-of-pocket dollar cost, this was a big one. I’m still not done fixing/replacing stuff, and stopped tallying up the total 2 weeks ago. Found the bad elliptical machine just yesterday and wondering when I’ll finish finding fried electronics around the house.
Ha! I actually texted SharkWife the cost of the key and told her I was just going to buy a new car at the dealer - I sent a pic of a car and the pricing sheet. Had her going for a bit because this is totally something I would do.
I think you owe an explanation for the six cans of beer.
Biggest for me thus far was $1,000 for a crown for a broken tooth. Most annoying was just yesterday, an electric bill for one day, which was for 45 cents of electricity and $7 for the monthly service fee. It was for a house I just sold, and despite having the service changed over to the new owner on my last day of service on the previous billing period, they didn’t close out the bill until the next day. Fuckers!
Our kitchen sink wasn’t draining, a continuing problem. Draino did not help, so we called the pliumbers. The pipe was almost totally blocked by scale - in fact our entire drainage system, which was 65 years old, was blocked. (We got new sewer lines a few years ago.) Cost was close to what we paid for our first house.
I don’t count medical expenses as unhappy costs. 'Cause I am happy when I am well.
Timing belt for the Outback and I am doing a whole engine rebuild on the Road Kow because all my followers were pretty much worn away. Since I have to yank the motor anyway --------------
(the good side is while I’m in there I’m doing the whole Screamin Eagle thing)
$7500 to replace the main sewer line to our house. Tree roots grew into it & if the damage was 3 feet further -on the sidewalk instead of in our yard-the city would be responsible to repair it 
That’s how I felt about the 4-figure bill I got before I met my deductibles. Money well spent, IMNSHO.
The $400 or so that I paid my vet to euthanize one of my cats in March was definitely an unhappy expense, but he was very sick and it had to be done. 
He was about 18 years old.
I bought a truck last week, and had to pay $150 to California to get a title.
Still got an awesome deal. 
But that California thing really sticks in my craw.
Too late to falsify property survey records for the house by 3 or so feet? 
I’m kind of waiting for this to happen to us - 100yo house surrounded by massive, ancient trees.
A round of IVF…about $16k all told.
Not as bad as most of the posts here but I was really annoyed when the windshield on my three month old car was cracked and I had to spend over $300 getting it replaced.
Yeah, I’m starting to feel pretty goddamn petty. :o
Back surgery: $5500.
New used engine replacement for car: another $5500.
Had hoped to fix some big plumbing issues (including breaking and then repairing outside concrete basement steps to access sewer line) for yet another $5500, but that’s going to have to wait. Ditto on the new windows.
I always hate paying personal property taxes. We get to pay in 2 different counties. And Mr.Wrekker has too many motorized vehicles. A boy and his toys, oy vey.
$20k for a new air conditioning system. The old one was over a decade old and was failing and economically repairable. On a positive note, my kids are now comfortable sleeping in their rooms all year long since the new system is a heat pump so they have additional heating in their rooms.
Two:
An MRI to determine that a problem with my left hand wasn’t going to kill me or result in extreme unpleasantness - $800 was my share.
More recently, an emergency move from my old home of 20 years to a new place - cost of new lease on a place with less room and more monthly cost (but, OK, better neighborhood), cost not totaled up yet (move is still underway - I’ll be sleeping on the floor until Wednesday when my bed and other Things Too Big For Me To Move) but it’s well into the thousands.
While out boating in March, I noticed some strange vibrations. These got much worse and I barely made it back to the dock. I asked the marina mechanic to come have a listen and when I asked “What does that sound like?”, he said: “Expensive.”
Sigh. A transmission gear had sheared somehow, and the metallic parts circulated through the entire thing, grinding and damaging every bearing, shaft and gear. Total replacement was required, with the bill topping 10K. This was not a fun purchase.