Our old ('73) 30' Tartan still takes us where we want to go and brings us home again. I've managed to get FW cooling and a heat exchanger on the old Atomic 4, but the Admiral resists such things as shore power, pressure water, and hot water. I was able to talk her into a chart plotter this year - Lowrance HDS-5, and we've both enjoyed it. Good addition.
Also had a bout this fall with the manual bilge pump. Wasn't working right. Investigation found several problems. Diaphragm in the pump had a small hole (not surprising, 38 years old), broken hose clamp (perhaps allowing air into the suction line), and a deteriorated suction hose with a small split between the corrugations (that old grey stuff). Rebuilt the old Guzzler (says Dart-Union on the back), installed new hose, new hose clamp - now pumps like a champ.
I suspect a lot of folks with bigger boats and more 'systems' get overwhelmed with maintaining the stuff. Mechanical, plumbing, electrical. They can't do it themselves, can't afford to have a yard to it - and the boat goes to pot!
Anyone else out there in the 'stay small, stay simple' school?