I've been mostly lucky with my house, stuff that broke was just regular wear and tear items. Weeping tiles was the big one and it happened early on too. But costs of living were way cheaper then so I guess it's better that I did that like 10 years ago, vs now... The cost would probably be like double and I have way less disposable income to put towards paying something like that off, than I did back then.
Furnace broke down last year so that was not fun, but was surprisingly not that expensive. Around 4k if I recall. My heat pump water heater which I decided to do at same time actually cost more, that was around 5k. Looking back I should have just bought and installed myself, would have saved myself 2k. I'm already noticing a big savings on my gas bill though, and hydro did not go up that much.
Next big thing I need to do with this house though is the roof. It's due in 2026, after that my insurance won't cover me if I get any issues as a result of roof failure. I was doing work up there and it looks in decent shape overall, but the north side is really showing it's age. The shingles are graying (suppose to be brown) and there's lot of moss. The adhesive is also not holding down anymore. So next year I will look at getting that done. Roofing is something I rather hire out than do myself, it's hard work, usually involves working in the heat and you're also racing against time to get it done fast before it rains. It would take me weeks to do and I'd be dealing with tarps and worrying about water getting in all the time, a roofing crew will have it done in a day.
I'm like 25k in the hole right now after the furnace, water heater, and getting my off grid land cleared and doubt I'll pay that off by next year so not the best timing to get the roof done but better safe than sorry. I have like 25k in company stocks, I just can't take those out fully yet, so I'm kind of banking on that getting me ahead in the next few years when they are available to cash out.