Note the condition clearly
Track location, timing, weather relationship, and prior work. Photos and rough measurements make the first conversation go further.
Read the local context
Walk the elevations before anyone quotes, because they will not all need the same work. Under mature pine canopy the shaded sides hold moisture long after storms and the recurring failure there is mildew rather than fading -- painting over it seals the problem in. Establish the age of the house and what is under the current finish, since older in-town wood substrates can carry layers whose age governs how the surface may be prepared. And if the walls are unpainted masonry, think hard before starting, because that decision is close to irreversible.
Ask what will be hidden
Humidity trapped in the substrate, chalking, failed caulk, and long hours of direct sun determine the real preparation and coating plan. A written scope should explain the prep and verification work that won't be visible when it's done.
Weigh whole scopes, not totals
Check protection, access, materials, permits, testing, cleanup, restoration, exclusions, warranty, and change-order terms.
What official local sources add
This is the trade local designation touches most often, and it catches people by surprise because painting feels like maintenance rather than alteration. On a designated property, changes visible from the street can be reviewable, and that can extend to color and to finish on trim, porches and siding -- so confirming status for the specific parcel before purchasing anything is the cheap step. The stormwater program has nothing to say about paint. What it does bear on is site work incidental to a repaint, such as regrading or replacing a walk while access equipment is already on site.
Checked in 2026, flood zone, historic-district status, and permitting still need parcel-specific confirmation with the City of Columbia.