Let's see ...
Chimney in kitchen has a rusting metal insert installed when home was built (late 70s) so fireplace there is useless -- cost to fix vs. cost to install gas fireplace instead were about the same when we were quoted about 15 years ago. Solution? We occasionally light candles in it ...
Roof done about 15 years ago, so I ask the contractor about the shed in the yard -- he says it is fine. Well it isn't fine any more and getting a crew in just to do a shed is overkill. Not sure what I am going to do about that one, but will have to do something this Spring
Trees -- I have already killed eight (in fairness, one blew over before I could kill it). I have planted two small ones (a conical fir and an ornamental pear) which didn't cost me very much. Cheap tree removal crew (first and last time I used them) slightly damaged the eavestrough at one corner of the house -- haven't fixed it yet, but I will need to this Spring along with the shed roof. Cedars ringing the back yard (about 16 feet tall or so) are expensive to maintain (annual fertilizing and trimming -- they are too tall for me to trim myself). To save the cherry trees along my driveway I had the sod removed and planted periwinkle -- the roots were coming above grade and making mowing an adventure. Crappy tree out front is owned by the town and it is dying -- I hope they take it down before it comes down on my cars ...

Raccoons -- wife made me pay the expensive "humane" removal price; follow-up costs included caging up every possible house orifice that isn't a door or window -- you might be surprised to find out how many of those there are in the average suburban home
Pool -- kid-safety fence installed and subsequently discarded (they are old enough not to wander into the pool any more); liner replacement; drop-in stair replacement; filter and pump replacement; brominator replacement (twice); winter cover replacement; diving board replacement; leaky return line trenching/repair. Oh yeah, pools are a bitch ...
Motorized awning affixed to back of house over pool patio -- canvas replaced once and housing constantly needs re-bracketing
Toilets. What is it with toilets, anyway? We have four and I have outright replaced 3 of them (but not before replacing the innards of all of them several times) -- I am sure replacement number 4 is not far off ...
Windows -- all dining room and kitchen (but one crummy slider over the sink) replaced, the latter including two large trapezoidal custom jobs
Flood -- this was the big one. Under-sink-mounted water filtration system sprang a leak while we were out for dinner -- ruined kitchen, dining room, living room, powder room and first floor hallway floors along with the
entire finished basement. Fortunately I had a plumber do the installation of the faulty water filter, so my insurance covered the $40,000+ gig