I've lived in my circa 1961 house for 5 years (bought at age 51). Prior to that, I lived in a 1993 house that I bought in 2003 (bought at age 10) and lived in for 9 years. Here are the areas I have, and have not, performed work:
1993 house:
1) All the builder's grade appliances died within those few years: HVAC, dishwasher, garbage disposal, fridge, stove, garage door opener with plastic gears, water heater, etc. $10k total? IDK. The HVAC guy told me the old system struggled because the intake was undersized and the house is almost all flex-duct.
2) The builder's grade aluminum double-pane windows felt like single-pane in the winter. Vinyl siding made storm windows not an easy option.
3) The roof was planked in OSB and sagged so you could see each rafter. Technically this caused no problems, but a falling tree limb once poked a thumb sized hole right through!
4) The posts supporting the deck, which was 15' above the back yard, apparently migrated with time and were no longer level.
5) An add-on over a previously covered deck had constant problems with drywall cracks.
6) Bricks next to the driveway started cracking out because nobody had installed an expansion gap between the house and driveway.
7) By age 12, the vinyl flooring and carpet were unbelievably nasty. I replaced all the flooring in the entire house. $7k?
8) Added 2" cellulose over the original 6" fiberglass insulation.
9) Water started pouring through a light fixture during a thunderstorm. Traced it to a deteriorated vent pipe rubber boot.
10) Water and debris would flow down the driveway and into the garage.
Few/Zero problems: wiring, plumbing, sheetrock
1961 house:
1) The HVAC from the early 90's was toast. So was the ductwork, which was caked with hair and dust on the inside. $18k to redo it all with top-of-the-line.
2) Previous owners failed to use treated lumber on the covered back porch wall with screened windows which was an add-on. The whole thing crumbled as I dismantled it. Replaced with anchored treated posts, railing, and redid vinyl siding on that whole wall. $1,500 in materials and many hours labor and research.
3) Added 3 whirly vents because attic ventilation was insufficient.
4) I have a brown/pink bathroom that is hideous. Next project!
5) Prev. owners redid a bath with white grout in the 90s. NEVER USE WHITE GROUT FOR ANYTHING.It cannot be kept clean. Good god, think people!
6) Prev. owners added onto the back of the house with a low-slope roof. It now has wrinkles in the shingles. One leak occurred during a thunderstorm where the add-on joins the old roof and creates a flat spot.
7) A pinhole leak occurred in my copper kitchen sink drain. Replaced with all-plastic for $25. Detergents or foods corrode copper, which is why it is no longer used for drain lines.
8) Back deck needs replanking due to age.
9) Replaced all outlets in the house because they were so loose plugs would fall out. The insulation on the 12-gauge 2-wire ungrounded cables was in good shape. Installed childproof outlets, so no need for covers! Not to code because the new outlets still aren't grounded, but not a problem either.
10) Crawl space floods because outside ground is higher. Adding french drains soon.
11) Added 6-8" cellulose over existing 6" fiberglass and rock wool. Utilities are very low, house is very quiet, and the HVAC is likely to last much longer now.
12) Nails are backing out from under the sheetrock in various places, making bumps.
13) 1960s sliding doors suck! Openings are not wide enough to replace with real doors. Ugh...
Few/Zero problems: hardwood and tile flooring, circa 1980's? garage door opener, wires themselves, vinyl replacement windows, cast iron sewer lines
THINGS TO AVOID OR AT LEAST SCRUTINIZE:
-flat or even semi-flat roofs
-add ons: 99% are badly done
-copper drain or sewer lines
-copper gas lines
-10 year old appliances
-particle board under carpet
-old HVAC systems
-water heaters older than 5, esp. if flooding would cause damage
-subfloor rot in bathrooms
-galvanized steel water pipes
-unlevel floors
-HVAC or water heater closets too small to install high efficiency replacements.
-Undersized HVAC air intake.
-Inaccessible parts of the crawl space or attic.
-Note that replacing flooring surfaces can be more expensive than more intimidating repairs, such as foundation work or a new sewer line.