Sissy Lifestyle assignments are for sissies that have come to embrace their inner girl. And while you might not be ready to shout from the rooftops that you are a sissy, you're ready to invest more of your time and money into her needs (after all, if you spend $50 on clothes in a month, how fair is it that she gets nothing?).
Women generally have finer body hair than men. It is also thinner and grows in fewer places. For instance, women do not generally get hair on their breasts, whereas a hairy chest is often a sign of manliness (and many men have hair around their nipples). Underarm and leg shaving is all the rage throughout the world (for women - so that means for you too, sissy!) - whether for aesthetic, athletic or religious reasons.
For this sissy lifestyle assignment you are going to spend the winter keeping yourself shaved like a woman in the most inconspicuous places. The first day will certainly be the most daunting, since you'll have the most work (as you end up shaving more often and with more skill it will go faster and require less clean up). You can remove the hair any way you like, but I very much recommend against an electric razor (it's easier to get razor burn and the shave isn't close).
Shaving is best done in or right after a shower or bath, when your pores are open and the hair follicles are most accessible. Since most sissies don't have the funds or courage to go for full facial hair removal you might as well start there and shave normally. For the purposes of this assignment you are going to shave your legs and your underarms - the two (and, in the winter, very clandestine) parts of your body destined for feminization first. If you're very hairy, or a more courageous sissy, you should also shave your chest and back.
(I haven't included the pubic area since that is up to you - a woman's or sissy's decision to shave down below is her own preference (but may I recommend a heart shape? :D)).
Leg shaving can be very tricky, so you may want to consult a wiki. Remember that if you have a fresh, sharp blade you really don't need any pressure, just pull the blade gently and smoothly along the skin. And if you have sensitive skin or skin prone to in-grown hairs, shave with the grain multiple times instead of shaving against the grain (for the legs, this would be downwards instead of upwards).
Of course, now you'll need a normal shaving schedule, sissy!
Many women shave their legs every 3 to 5 days since leg hair stubble becomes more noticeable after about 72 hours. You'll certainly want to match their feminine routine. Every 3 (or 4 if you want to set it to specific days of the week) you are going to shave your armpits and your legs. And you're going to continue that routine until April.
Of course, by then you may be so locked in your routine that you won't have any inclination to stop. After all, you could always claim you're shaving for other reasons in addition to becoming a better sissy!