I live in a house built in 1927. We THINK it is a Sears home, for whatever that is worth. Chicago suburb, so not the same concerns a a rural community.
Lets start with the good about my house: Windows were replaced probably 10-15 years ago. The plumbing and HVAC are most certainly not original. We think the bathrooms were redone about 25 years ago, and the downstairs one had a light remodel again maybe 15 years ago. There are parts of the house that they put drywall up, and in the rest of it the plaster is in good shape. The garage was built in 2000, in the past 15-20 years someone spent a ton of money on insulation in the attic.
Now the bad.
The layout sucks for tv viewing. There just is not a good way to set up the tv and sofa/recliners. We do not watch a ton of tv, but it is an annoyance. We cannot fix this without significant remodeling.
The layout in general is odd. King sized beds were not a thing. People back then had 2 suits and 2 work outfits and pajamas. Accordingly our closets are tiny. They built a room into what used to be a crawl space, it is 8x8. The closet in that room is uninsulated and 4x8. Yeah, the closet (with sloping ceiling) is half the size of the room. The master closet is about 3x2. Another bedroom is about 8x20. In that bedroom, you looked at the chair rail and thought... why is there a chair rail in here, and why is it that high up? Well, I’ll just pull it down when I paint it. Pulled it down and you saw how someone had no clue what they were doing when hanging drywall. Ok, guess I’m buying a nail gun and putting in a new chair rail.
On a house this old, unless there was a gut rehab, you’re going to find really annoying things. First of all, NOTHING is square anymore. This is true of new homes too, but it is really true of really old houses. Then you’ll look at the obviously redone bathroom and wonder, what the hell were they thinking? And you’ll look at that for a lot of stuff in the house and wonder that. In my house I do it in the kitchen, the basement (why would you finish two rooms of the basement, but you have to walk through the unfinished part to get to them?!), the upstairs bath, and the upstairs bedroom.
I have a bedroom that has 1 plaster wall, and 3 walls that are drywall hung over plaster. If you’re mounting something to the wall, that’s something that you need to know - gotta drill a long way to get to the stud.
For any house, as things age they’ll wear out. I keep water valves in my basement because they all keep failing eventually. I should just replace every one. The electric is all good and updated... except for that outlet, don’t use that outlet guys. Need to fix that, but it’s a roundtoit that is still on the list.
We’re happy with our house, but the fact is if the windows hadn’t been replaced already it would have been torn down 10 years ago when it sold last before us buying it 4 years ago. Go price new windows - and sit down before you look at it. Same goes for the bathrooms and the kitchen - and they all really could be redone now, but they’re at least functional. Small though.
These things aren’t on every old house, and the good parts of my house aren’t either. Every one is different. But when I think of my grandparents house that was built in the 50’s, my parents house built in the 60’s, or the house I grew up in built in tbe 70’s, I get “jealous” at a house that would just be slightly easier. And then I look at my in-laws McMansion built in the 90’s with a E36 M3ty layout and wasted space and poor build quality and I’m happy again with our old bungalow.