Lots of good advice already. Just wanted to add another +1 for the quality of build being as, if not more, important than the wheel components. Properly trued, tensioned, and stress relieved, entry or mid-level wheel components can hold up amazingly well, but a poor build can make a bad wheel out of the best components. Find a good wheel builder and have him/her detension and retension, true and relieve the wheel. Unless the rim is actually bent, chances are it will last a long time with minimal if any retruing.

If your wheel has needed retruing multiple times in a month something is wrong. Even an entry level wheel should hold up better than that. If Performance has been repeatedly truing the wheel without checking and balancing the tension and stress relieving it, they are possibly making the situation worse, not better. Many inexperienced shop mechanics underestimate the importance of even and adequate tension and will either just pluck a few spokes, or spot check with a tensiometer and pronounce the tension "good enough" as long as the wheel spins true.

Once your wheels are properly trued and tensioned, and if your frame clearances allow it, consider a higher volume tire if you are going to commute on rough roads or paths. Not only do they give a better ride, they reduce the chance of pinch flats and provide some additional protection to the wheel. Even going up one size such as 25mm > 28mm or 32mm > 35mm will make a noticeable improvement for a slight weight penalty (not a problem for a Clyde on a loaded commuter).