You're not careless about your property. You maintain it, you budget for it, you lose sleep over it when a storm rolls through or a contractor gives you a number that doesn't feel right. The problem isn't that you're not paying attention. The problem is that every professional you rely on for information has a financial interest in what you decide to do with it.
Your contractor profits from the scope they recommend. Your property manager is optimized for operational smoothness, not capital preservation. Your insurance adjuster works for the carrier, not for you. And unless you have independent data in your hand, every conversation you have about your property's condition, its capital needs, and its risk exposure starts from a position of disadvantage.
That disadvantage is quiet. It doesn't announce itself. It shows up as a repair estimate that feels high but you can't challenge it. A reserve fund that turns out to be underfunded when the roof finally fails. A storm claim that gets settled for less than the actual damage because you filed without documentation. A capital project that runs over budget and over schedule because nobody was watching the work independently.