Pay Now or Pay Later

There used to be a commercial for Fram oil filters built on the theme of "pay me now or pay me later." A mechanic was rebuilding an engine that he says wouldn't need rebuilding if the owner had used Fram oil filters. The message: you can buy a Fram oil filter from him now or an expensive engine rebuild from him later.
Cute.
I don't know if it is true or not (although I religiously bought Fram oil filters for the next 30 years after I saw the commercial), but I do know there is a corollary in real estate: It has to do with updating your house and it goes, "You can buy it now or you can buy it for someone else, later."
Here is how it works. You are not planning on moving any time soon. Your kitchen is dated. Should you spend the money to update it?
Quick answer: Yes. If you would like the new kitchen and if you can afford it. (And you should really try to afford it.)
If you do not update your kitchen, when you do sell - off in the future somewhere, - the market will discount the value of your home for the out of date kitchen. The long term reality is you are going to buy a new kitchen for somebody, someday. It probably ought to be you, don't you think?
The same goes for outdated carpets, beat up trim, unfinished basements, bathrooms that need fixing - the list goes on and on.
Now, it is possible that the discounting won't be dollar for dollar what you would spend, and certainly, you can't expect a dollar for dollar return in increased value when you update, but in general, updating is worth it - especially if you will enjoy your house more between when you upgrade and when you sell. And when you take into account inflation and the increasing cost of doing anything, it is really worth it. Anything done today will cost less than the same thing done several years from now.
So when people ask me if they should update the kitchen or finish the basement my answer is always yes - because you're going to pay for it in the long run anyway. So you might as well enjoy it yourself.