The route up to Woodland Park on Hwy. 24 is problematic. Narrow, busy, sometimes pretty scary. There is some chance to use an alternative route part of the way, but not all of the way. So that part is kind of tough. The route from Woodland Park to Deckers is really nice, there is even a bike path part of the way. The section you have mapped out from Deckers to Pine Nook is dirt road. I don't know if that's a deal breaker to you or not. The biggest problem I see with your route, other than it being quite challenging, is the section from Sedalia into Denver on hwy. 85. I think this section is quite dangerous, or has been -- perhaps it has been widened or something but last time I was on this road it was very unfriendly for bikes. I'm not aware of any nifty ways to avoid this road other than altering a substantial portion of the route by heading north out of Deckers to Buffalo Creek and Pine, then using one of two or three routes to climb to Hwy 285 then down 285 to Meyer's Ranch and up and over to Deer Creek Canyon. That will deposit you in extreme southwest Denver, where you can use bike highway-like MUPs to take you into the city core. That's some tough riding but doable. It may also be possible to zig east from Sedalia and pick up a more friendly route north into town from there, but I'm not sure of that.
The traditional route along the front range (just east of the mountains but still in the rolling foothills) uses a fairly smooth and fast dirt path from north CS to Monument through the Air Force Academy, then Perry Park Road from Palmer Lake to Sedalia (where you will again have to figure out how to deal with 85). This rolling road passes through some beautiful country; traffic can get pretty bad at times but not too bad by the standards of this rapidly suburbanized area. Douglas County has been one of the fastest growing counties in the country for a few decades, which is to say it used to be empty other than working ranches, now it's full of ranchettes.