It took us years to compile the list and it’s paid for itself many times over.

But to jump start the list in a future place, especially a traditional house, I’ve considered hiring a housing inspector or general contractor to give us a walkthrough of key maintenance timelines. Many things could be decades away but easy to forget until it’s a much bigger job. Notes from that interaction would essentially be the bones of “the list.”

That's a rough one. I know a good place to start is anything large you buy, make sure you read the maintenance portion of the manual and make a couple notes.

Then I start asking myself about important things like "how do I make sure the plumbing doesn't get fucked? " or "how do I make sure the furnace doesn't die?" and I start googling.

Not a great answer but it helps. I recently realized I didn't give much of a thought to well pump maintenance and I've been down a massive rabbit hole on that one. I feel like you just pick one thing at a time and work on it and you learn as you go.

Just follow Martha Stewart's website, you'll find there are several thousand hours worth of chores you should be doing weekly!