Congrats on the new role, Mark! If you end up forming a committee, I'd be glad to help create or compile maps if needed.
Here's my 2 cents on mapping software and some online mapping services I have bookmarked:
mapmyride.com
Plagued with ads and costs $5/month to print some very nicely formatted maps and cue sheets, but otherwise free and easy to use and provides just about everything you could need. Features: elevation profile, GPX and TCX files, search routes by city, cue sheets, automatically follows roads, total ascent/descent. One really nice feature of mapmyride is that it includes Google Street View which allows you to actually see road conditions, intersections, scenery, etc. on your route.
bikeroutetoaster.com
Free but donations accepted. Does about everything mapmyride does and allows preset warnings for turn-by-turn directions in GPS files. As with any Google Maps based service, printing a good looking map on which you can actually read the street names is challenging. I've not found the ability to search routes by city and link directly to a route like you can with mapmyride. Does anyone know if this is possible? This would almost be a must for club use since we would want a link to a route on the club website.
These sites are similar but I don't have much expereince with them. They might be worth considering.
bikely.com
ridewithgps.com
gmap-pedometer.com
The best printed maps I've seen come from software packages like Delorme Topo or Microsoft Streets & Trips. A nicely formatted printed page with visible street names and a highlighted route is sometimes hard to produce with a Google Maps based online service. Some of our ride leaders have provided great maps by copying the TN Atlas and Gazetteer pages, too.
As far as other club examples, I like the Veloteers route maps. They've done a great job using Delorme Topo and have posted two page pdf files that have a map, cue sheet, elevation profile, ascent/descent data, etc.
www.veloteers.org (navigate to "routes" on the menu)
Here is an example of one of their route sheets: http://www.veloteers.org/images/maps/NHBC/NHBC 28.86.pdf
Maybe we should define the set of map/cue sheet requirements that the club needs and then figure out a way to combine the best of an online service with a printed map software package to produce both a pdf download and links to an online map and gps files for club members.
I'd be interested to hear what software/sites others are using. Anyway, sorry for all the rambling... hope this helps!