Absent faulty installation or materials, a tile roof should last indefinitely. If you do develop a leak, it should be repairable without a complete roof replacement.
I don’t see why you would expect to re-stucco either.
Nor would I expect a need for a wholesale window replacement. San Diego has a very mild climate so economics do not dictate a need for high efficiency windows. You might want to replace a couple of windows or sliding doors that have seen heavy use.
Absent, a gross failure, pool resurfacing is purely cosmetic.
Basic builder new construction kitchens are nothing to write home about either. Unless the kitchen is literally falling apart (and I have seen some that are), the need to spend $25K refreshing it is fairly subjective.
Bathrooms are pretty much the same absent a tub failure.
I draw a distinction between “deferred maintenance” and “dated”. If the roof leaks, the stucco is falling off the walls, the windows won’t open and the doors don’t close, the pool plaster is collecting on the bottom of a pea green pool, the kitchen drawer fronts and cabinet doors are falling off, only two range burners work, the tubs are all rusting through, the original color of the floor is unclear, the furnace won’t run and the water heater drips a stream that is running out a garage door off it’s tracks, you have “deferred maintenance”.
I think most buyers have some understanding that these things will be expensive. They may have skills or relationships that allow them to cost repairs differently than you do. You might see $25K of window replacements and I might see $200 of parts and a weekends work.
If you you personally need all these things to be new, you should probably focus on new construction.
