My Pro Coach training plans range from 6 to 40 weeks in duration, so the best thing to do is count back from your "A" target race date and then choose a plan to fill that gap. You can fit your other races into this timeframe.
The training plans take you right up to your race day. The longer the plan the easier it starts and the more gradually it progresses. So that has a bearing on the difficulty level you choose. For example, a 12 week plan starts off at a higher level than a 36 week plan because with 12 weeks left there's not as much opportunity to build up slowly.
What about when you have two "A" target races in a season? Which training plan should you pick?
If the two races are within 10 weeks of each other, you should choose a plan targeting your longest event (the more weeks the better) as this will also get you in great shape for your 2nd event.
If there is a gap of several months between the two races, you could choose two separate plans each specific to each race.
All the training plans include speed work, so a long distance plan (for instance) will still get you in great shape for a shorter event.
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