I've done Pikes dozens of times as I live down in the Springs and the Thon last year. Anyhow, don't underestimate going up to 14k feet from Sea level, that has a lot of potential to F you up. That being said, some people can pull it off and be okay coming from sea level, just be aware you can get nasty crap happening to you like bad tunnel vision/lightheadedness. I would recommend you bring plenty of water as you dehydrate big time with how dry it is up there, once at the top you can get plenty of water for your hike back down. Crags is the Pu$$y route by the way, so i think you should be okay , its a lot easier than going up via barr though its steeper in spots and more "stairstep" like in certain points of the Cragg route. You need to be extremely aware on what time of day you go up as afternoon showers can be really dangerous up there if you get caught in a lightning storm. I recommend if you want to do the trip that you head up first thing in the morning.
Lastly, if you're in Woodland I highly recommend you go up to Rampart Reservoir to get runs in, its a great place to train, you can take Rampart range road all the way from the rez down to Garden of the gods.