Right now I'm living in a smallish house that's about thirty years old. I've been living here for about a year.
The previous owners did very little maintenance, pretty much only fixing things up after they'd already broken.
Off the top of my head...
1. Neither of the doorbells work. The button for the back door's bell is actually cracked and broken, so there's now semi-exposed wires. It's on my to-do list, as I'd hate to fry a Jehova's Witness or something.
2. The house hasn't been painted or anything in probably fifteen years. The paint is faded and chipping. The wood looks like it's falling appart (I'm frequently finding nails that have fallen out of the side of the house).
3. The wooden back steps also haven't been painted or anything in probably a decade or so. Again, the wood is looking pretty damaged, and nails frequently pop out of it.
4. The insulation in the basement was installed incorrectly. The fiberglass is facing downward, exposed, rather than up toward the floor.
5. The basement floods when the snow melts in the spring, and whenever there's particularly heavy rain. This is likely to be even worse next spring, as the town just cut down a whole lot of trees behind the house to put in a new road.
6. Many of the kitchen cabinets and drawers are damaged beyond simple repair.
7. The kitchen sink occasionally has leaks from the pipes under the counter.
8. One of the upstairs ceiling fans doesn't work, and lightbulbs that are put into its lights tend to die exceptionally fast (within a few weeks or regular use).
9. There's visible water damage on the ceiling in one of the bedrooms.
10. There's visible water damage on the ceiling in the downstairs bathroom, right below where the bathtub is.
11. And this one's probably my absolute favorite. Fuckin' Squirrels EVERYWHERE. There's a vent on the side of the house that I suspect they're using to come in the house. You can hear them scurrying around behind the walls at all hours. There's definitely a few of them. On several occasions I've caught baby squirrels in Have-A-Hart cages in my kitchen using some of my cat's food for bait (and no, my cat has absolutely no interest in hunting them, because she's a total wimp). I've escalated my war effort on squirrels from drowning them in Have-A-Hart cages to chemical warfare. I managed to get them to eat some poison a month or so ago, and I stopped hearing them in the walls for a few weeks. Smelled some pretty foul decomposition for a couple days, but then it was peace and quiet. But as of two days ago I can hear more scurrying around in the walls, despite having put a metal mesh over the vent I thought they were using to get in.
I can't wait until I can afford to get the hell out of here, because I certainly can't afford to repair all the crap that needs to be fixed, not to mention pay for an exterminator.