How do I know it is actually time to upsize?

Knowing it is time to upsize usually comes down to a genuine space need, like a growing family or a home office you cannot fit, combined with the numbers actually working: enough equity in your current home and a monthly payment on the next one you can comfortably carry. Running your current equity against current interest rates on a larger loan, rather than just wanting more space, keeps the decision grounded. A pre-approval for the next home clarifies what upsizing would actually cost monthly. Joel Boss can run that comparison with your real numbers before you list.