I'll now attempt to chronicle my new journey to upgrade to USA Cycling Category 3 Road racing.
http://www.usacycling.org/road-category-upgrade-guidelines.htm
I've sketched out the next few months of training using a new, low cost eBay purchased custom built wheel using a 16 hole PowerTap SL+ hub which was laced on a Bontrager carbon rim. With this, a basic Ascent fluid trainer ($129 @ REI), and a $12/month subscription to TrainerRoad, I've got my training set.
I've looked a a variety of training programs and the base building ones from TrainerRoad seem to work just fine for a enthusiast like me. Find me over at Strava: https://www.strava.com/athletes/1428675