Building up instead of out, on a foundation and main floor that were not necessarily designed to carry it.
Adding a second story starts with an engineering question, not a design question: can the existing foundation and first-floor framing carry the additional load, and if not, what reinforcement does it need. This is the step people most want to skip because it costs money before a single wall goes up, and it is the step that determines whether the rest of the project is even feasible as imagined.
Once that's answered, the project becomes sequencing as much as building — the roof comes off, the house is exposed to weather for a stretch, and the homeowner's daily life and the builder's schedule have to line up around that window. A builder who does this work regularly plans for the exposure period deliberately rather than discovering it mid-project.
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