+1

The primary factor in wheels staying true is sufficient and even spoke tension, which comes down to the quality of the build, but having more spokes allows for a higher margin of error. A skilled wheel builder could make a 24-spoke wheel that would stay true for you, but anyone with a spoke wrench, a truing stand and Jobst Brandt's book could build a 36-spoke wheel that wouldn't give you problems.

I would also note that having to take a wheel in multiple times for truing is a sign that the underlying problem probably hadn't been addressed. Most bike shops offer a cheap wheel truing service that typically amounts to taking the wobble out of the wheel by making adjustments to the spokes near the hop. Any mechanic in the shop can do this. However, the wheel probably went out of true in the first place as a result of uneven spoke tension. Checking for this and correcting it is a bit more involved and would probably cost you more, but the long term results are better.

I've had good luck with Velocity A23's. I weigh 200 pounds and have a set of 32-spoke A23's that I built myself. I've used these for everything from road rides to cyclocross racing and they've held up. They're now available in an off-center model too, which makes for a stronger rear wheel. If you want to reel in the budget, the SunRingle CR18 is a rim I've heard a lot of good things about.

In terms of value, you can't beat Shimano hubs. Any 10-speed hub will work with 8- or 9-speed cassettes as well. I think the Tiagra level is great quality for commuting. There's not a lot separating it from 105...maybe just weight and finish.