This is the reason new builds out in the burbs close to public transportation are going for the prices they are.

My next door neighbor keeps doing cosmetic outdoor things (and indoor it seems) but is ignoring the hole on the side of her roofline which has a family of squirrels and some birds making the attic space into their home… not smart but it’s her house I guess.

I’d do what is going to be best for you - either to help you sell down the line or help you live safely and happily inside your house.

The structural issues need to be addressed. It’s not fun, but sometimes you have to prioritize those items before moving to the sexy stuff.

Do you intend to stay in this house short/medium or long term? If you anticipate moving in the next ~5years the cosmetic updates might make more sense for return on investment. If longer, probably you need to
bite the bullet and do the longevity structural things first. Anecdotally, do it all as soon as it makes financial sense for you to do it, vs putting it off. My parents lived in my childhood home 25 years, and only did it all right before selling. I thought it was unfair for them that they did all the upgrades (air conditioning installed, wood floors, re-painting for the first time since moving in..) in the last 3 years before selling. They didn’t really get to enjoy their efforts they had wanted for such a long time to make.

We addressed safety and structural issues first, as well as replacing systems that were reaching the end of life. It sucked to have to wait another 5 years to get to the cosmetic work but we could breathe easier this way.

Start with one bit at a time and prioritize.
I would start with HVAC.

You’re not wrong. There are definitely moments in a house’s life where a full overhaul is called for and your house may be there.

I don’t think this makes doing just a kitchen or bathroom necessarily a bad idea, it just makes it a bad investment. If you want to do it for yourself to enjoy while you live there, fine. If you care about the ratio of the renovation to the resale value of the house, maybe not.

NP here—
We have a similar situation. Our “list” is made up of many fundamental, not exciting, projects. To spend $$$$$ on those and never really getting the funds to continue on to, say, an exciting landscaping project..is hard to face.
Even the landscaping project is very practical, not just for beauty. (We have beautiful landscaping due the previous owner, however, it’s too much for us, some trees’ health is not good, and it’s leaving no room for plants we really love. In addition, movement of an installed fire pit makes sense for how we use our yard.)

But it has to be put off in favor of maintenance such as a porch/foundation question, reviewing gutters. Both will result in work and spending. Things like that.

We live in a rowhouse in Capitol Hill. When we bought out place several years ago, the plan was to eventually renovate it. The initial thinking was that we could just update the kitchen and bathrooms.

I now think that was naive. Our house has enough deflection on the second and third floors that it can make furniture placement an annoying process, and I now that that to make renovations worth, we need to address that issue as well (eg, by replacing or sistering joists). I also think we need to do things like replacing windows and maybe doors, updating some wiring and replacing our hvac system, which is old enough that getting someone to service it is becoming a pain.

Am I wrong to think that fixing up a kitchen and bathrooms is a waste if these other issues aren't addressed?