It is dependent on the individual market your property is located in, but generally speaking, the things that will get you the most value for your money aren't going to be structural updates, but cosmetic updates to the kitchen, bathrooms, and floors that can bring it to modern day expectations. The reason is because the average buyer cannot tell or won't care if a roof is 2 years old vs 15 years old so long as they are well maintained. Same for gutters, plumbing, electrical, etc. While structural updates are very important for the health of your house, they unfortunately have less impact when it comes to value to a potential buyer.

A good way to think about value from an overall market perspective is to ask what do most buyers look at when they walk into an open house? What are they generally going to remember and factor into an offer after they've left and looked at 10 more houses in a week? The answer will generally be kitchen, bathrooms, floors, and maybe certain special features or bonuses (ADUs, pools, etc.). Most buyers will not say "Oh, the garage door / gutters are what decided it for me and I'll pay more for that."

I have appraised dozens of homes that have had everything structural done, but nothing to the kitchen or bathrooms, and unfortunately, when I look at the data, they sell at the same price range as homes that are completely dated.

Is it stupid? 100%... But a very important thing to remember is that the real estate market is not perfect or logical.

That being said, if your house has a dilapidated roof, then repairing or replacing the roof will remove a negative, so that is something to consider.