If what you mean by "more user friendly" is "less intimidating to riders who may lack self-confidence on their bikes," then I think the more you can keep them out of traffic, the better. Can you find a different starting point on the edge of town (maybe rotating around the various areas, so it's not always a super long drive for someone who lives clear across town)?
The urban club I belong to starts all its rides in far suburban/exurban areas, so it's no more than 5 miles of in-town riding (each direction). But it's going to depend on your area, too.
Speed comes from what you put behind you. - Judi Ketteler