Timing is definately an issue with cattle...while I am not against timed AI like some people are, there are many situations which get tricky. Those times that different protocals list as when you should breed are just averages. Even when using drugs and synching to try at make the cows come in, all we are doing really is telling them to start a new cycle, and unfortunately all cattle dont cycle the same. So even if your vet is time AIing and is spot on with his protocal times, its still possible to not hit that cow at exactly the right time. I agree that I would prefer to just watch for a natural heat and breed on that. But again timing is an issue, you still have to have semen in them at the proper time, and sometimes its not possible to get to them at the right time. Thus the advantage of synching and timed AIing, I have had very good success with it and it actually allows me to create a schedule of when I am going to breed. If I bred every body I breed for cattle on natural heats there is no way I would be able to work out a schedule and get to them all at the right time.
Semen quality is always a culprit to consider, and as Zane said, I have had several in the past that just never would settle AI no matter how picture perfect the technique was. Yet they settled the first heat when out with a bull, everytime. I tend to think these are the same cows that maybe have weird cycles, the bull is more likely to cover them several times and get it done at the ideal time.
Keep trying, if you are doubting your technichian then try someone else. If she still doesnt get bred have some semen tested, and try a bull. If the bull continually doesnt get it done then its more likely a problem with the cow. Remember everything could "feel" great inside her and she still have something going on with her that is keeping her from sticking. For instance, if she is havin a hormone issue and not producing progesterone right, then your CL may be regressing and the pregnancy just isnt sticking. For things like that you cant necessarily feel the problem.