Goals for this thread are two-fold: Cautionary tale for perspective buyers and wondering out loud how bad luck we've had.
Picked up a 1986 M20J August 14th 2018 for $110K, 12 years and 1200 hours SMO. A couple of notes, the below is for two pilots getting their IFR ticket and about 140 hours total flight time on the plane.
Maintenance Costs in first year: $45,000
AvGas: $8500
IFR Checkride/Prep (2 pilots) other flying related expenses (memberships etc): $7400
Total: ~$60,000 first year costs (not including the plane itself).
Maintenance:
$3800 Pre-buy/Annual at pickup
$1100 Seat started to fail to lock -- Seat frame was broken.
$6200 Backup attitude indicator (turn coordinator replacement) started to fail, replaced with a G5, which when the pitot-static was tested failed the VSI, requiring an overhaul of the VSI.
$250 Battery died, stranding me (long distance uber required to get to where I was going not included)
$7200 VOR started failing, couldn't track down the problem, sent 530W to Garmin to debug, not issue found, ended up needing to overhaul the HSI and VOR #2. GDL88 had a failure where N number wasn't present in the FAA reports when filing IFR. New tire (my fault).
$9000 Stuck oil ring due to overheating issue, likely when we bought it appeared to have spark plugs that were not for the engine. #4 went offline in flight, EGT/CHTs were low, but quickly lost oil pressure. Landed without issue, but plane was not flyable, got 4 new cylinders from Lycoming and had the plugs replaced.
$8000 Install of new cylinders, Annual: broken compass bracket requiring remount, brakes were stuck on 1 side and didn't work, 2 new tires. Gas cap seal hadn't been replaced at last annual, but stated in log book as replaced, I state this only because I feel a lot of stuff was probably missed, or not looked at on a typical annual.
Other miscellaneous expenses not stated: Oil changes and minor issues
TL;DR: Planes are expensive or maybe we just have bad luck or we have been taken for a ride, check the spark plugs on the engine to make sure they match in the prebuy, if they don't assume they are using them to cover up a problem--good compressions won't mean you're in the clear for engine work.