I've had the usual broken cars, failed appliances, and leaky roofs. But here's what I hope is the worst case you'll ever see:
My father (in Grand Junction) ended up in the emergency room with a perforated ulcer. The surgeon saved his life, but it was clear that Dad's Alzheimer's was too severe for him to be able to live independently.
I flew in from Oahu, and my brother drove over from Denver. Dad was going to be discharged in about a week, and we needed to find a skilled nursing facility for his rehab-- followed by a full care facility. That's a full-time search for about five people in two different locations.
It took nine months for my brother and me to be appointed guardian/conservator. We did not have authorized access to his checking account (pension, Social Security) or his investment accounts. The hospital bills and the six weeks of rehab were paid by Medicare (and his supplemental insurance). However during that time we went as deep in the hole as $25K because the long-term care insurance claim was initially denied. Luckily that was later approved and retroactively paid to the start of his full-time care ($18K worth of paper checks) but we still had to shell out $6K up front for the next month's care before being reimbursed for the previous month's care. We paid over a thousand dollars for geriatric care managers (in both GJ and Denver) to talk through Dad's options and find a facility. Legal bills (lawyers for the probate court petitions, and a neuropsychologist to document Dad's Alzheimer's for the insurance company and the probate court) were over $10K. We also had to carry Dad's apartment rent and utility bills for several months while we searched all of his possessions (luckily he only had a 2BR apartment) and cleaned it out. We spent several hundred dollars on "miscellaneous" expenses like probate court interviews ("What makes you qualified to be a conservator?"), criminal background checks, and priority mailing of legal documents. Luckily I didn't have to post a conservator's bond.
I also had several thousand bucks in no-notice airfare, car rental, a night or two in hotels (until I got Dad's apartment key), driving Dad from GJ to Denver, and "surprise" expenses like getting his SUV caught up on its maintenance (and a new set of tires). I pretty much threw credit cards at every obstacle until people started saying "Thank you!"
Once I could legally access his accounts I reimbursed myself for the expenses. Luckily he has the assets for that.
Today he's 80 years old, he's been in the care facility for over three years, and he's doing as well as Alzheimer's will let you do.
I'm really glad that by that point in his life he was no longer a homeowner-- or a landlord.