In the beginning, my wife’s new hairdo wasn’t a perfect fit. As she was getting used to it, she identified trouble areas that she needed touched up so that it would work better for her needs. She went back to the salon once a week for the first 3 weeks until it worked for her. While it certainly seemed excessive to me (and to be honest, I warned her that her hairdresser might shave her just to keep her from coming back a 4th time) her willingness to keep at it until it was exactly what she wanted has saved her time in trying to make things work and retraining down the road since it eliminated incremental changes at every visit over the next 4 months.
Time and use will eventually expose problems in even the most customized solution, and certainly for stock out-of-the-box products. We may find that we need either custom work or additional parts/pieces/plugins to fully integrate a new solution to our business. Keeping our eyes open for early adjustments, and being ready to take the time to make the ones we deem necessary early on will help eliminated poor workflows and habits and reduce the pain of retraining. No one likes giving up one poor solution for another poor solution.