Each month's increase is not going to happen overnight. For instance, on the first of October I did not jump up to a 200-yard swim. I did a 150 and the following week I'll do a 200. Same for the bike. I am not going to have my last ride of November be 10 miles and my first ride of December be 20 miles. I will have worked my way up to 20 by December.
I think this is a pretty conservative schedule and I may have to adjust things along the way. For instance, if I am progressing really well I might want to turn my Sunday rides into specialized workouts (e.g. hills, one-leg pedalling, etc.). This is a good start, though, and it looks very do-able while still giving me flexibility.