Most exterior paint failures we see around Detroit weren't caused by cheap paint. They were caused by paint that went on when the siding was too cold, too damp, or too close to a night that dropped below 50°F. The finish skinned over before it cured, and two winters later it's peeling in sheets.
The realistic exterior season in Southeast Michigan runs from mid-May through early October. Even inside that window, we watch the forecast: surfaces need to be dry for at least a day, and overnight temperatures need to hold above the product's minimum, which is usually 50°F for standard acrylics and around 35°F for cold-weather formulas.
Morning dew is the other trap. Siding that looks dry at 9 AM can still be holding moisture, especially on the north and east sides of a house or under tree cover. We start on the sunny sides and let shaded walls dry into the afternoon.
What about the rest of the year? That's when we do interiors, drywall, and commercial work. If you're planning an exterior, the best move is to book your estimate in early spring so you're on the schedule before the good weather runs out.