Great thread. Travis's resentment audit is the right instinct. I'd add one step: put a number on the dread before you decide.
For each legacy account, divide the price per visit by the labor hours that visit takes, counting everyone on the crew plus the drive from the previous stop. Then compare it with the middle value across all your recurring customers. Two things usually show up:
1. Not every legacy customer is underpriced. Some early customers sit on your densest streets and turn out to be among your best earners per hour. Those are the ones worth honoring, like Anthony said.
2. The ones that hurt usually drifted on two fronts at once. The price stayed flat while the time crept up: beds added, a bigger yard, more rooms, a second person on the crew. Comparing this season's minutes on site with their first season makes it obvious.
So to answer the question: I'd move the ones well below your typical rate in steps (Travis's half now, half in six months works well), and skip the good ones at the next increase.
On Jobber, the Visits report shows the price per visit by date, so you can also see when each account last changed.
I wrote up the full method here: https://tinyurl.com/2j8rmzha. Full disclosure: I'm building a pricing tool for recurring service companies (independent, not affiliated with Jobber), so I'm biased toward measuring this. This document summarizes the findings I learned throughout the research on the topic.
