4:02 p.m. on September 19, 2012 (EDT)
Speaking purely of clothing I would bring, as I don't know which other gear is provided or not. I spent quite a few winter seasons in my youth camped for a month at a stretch at remote hunting camps. We would backpack in with pulks and set up a wall tent and stay for anywhere from 2 weeks up to a month.
So don't think of it as 'what you need to bring with you to be a caretaker', instead think of it as 'what do I need to bring for a prolonged base camping trip for the entire winter season'
I am not sure how you are getting there, vehicle, or walking, this may determine exactly how much weight you can efficiently get there.
For clothing, as a general summary, you will want three sets of baselayers, two changes of 'inside' clothes, and your clothing for venturing out into the elements. Some of these can be used together, and some cant.
Lets start with inside clothes. These are going to be items that are comfortable to wear for the majority of your stay, but wont see the outside except for short durations. These include things like sweatshirts, flannel pj pants, sweat pants, basically your favorite and most comfortable clothing that is also somewhat warm in nature. You may want to add a pair of gym shorts and a t-shirt or two.
For baselayers, these can be used in conjuction with any clothing system you bring, but should be performance in nature. I would recommend wool, polypropolene, silk, capaline, or other materials such as underarmor etc. You want two sets at least, but probably three. So this means tops, and bottoms. You will wear these anytime you venture out, when you need extra warmth inside, maybe even to sleep in. The reason I say to bring two to three sets is because you will be there for such a long period of time, this will give you the ability to get one damp/wet when working, change into a dry pair, and have one being washed etc. I assume you wont be doing laundry daily so this will give you a weeks worth or more before needing to wash.
Generally speaking when you go out into the elements, you want to be wearing a baselayer, an insulation layer, and a shell.
You only need one or two insulation layers, and only one shell. For insulation layers I would bring a nice down jacket, and either a fleece jacket, or some type of synthetic insulation layer, or a softshell. Down provides the most warmth but is succeptible to moisture, so since you are staying for a long stent I would recommend having something else along such as a fleece etc to either layer with the down under REALLY cold conditons, or to wear when you dont need as much insulation or when doing activities where you may get the down wet such as chopping wood etc from sweat. A nice fleece jacket can double in place of a sweat shirt for inside wear.
For a shell, you want a waterproof, windproof barrier to protect you and your clothing from snow/rain/moisture etc. These can be really expensive and fancy, or cheaper. There are so many options for this. But you want a shell, and not a 'winter coat'. A relatively cheap and effective shell would be to purchase a surplus ECWCS gortex parka. You can find these often for $60 or so, you can also get the ECWCS goretex pants for $40ish. Look for the old woodland pattern as these are now being replaced and can be very cheap on ebay or at surplus stores, especially used ones. Like I said there are alot of options, you can go to most any good outdoor retailer and look at a bunch and see what you like. Features that you amy like to look for, 'breathable', hood, pockets, thick enough to stand up to a little abuse. Some of them can be very thin and lightweight, and these sometimes sacrifice durability to reach these goals. The ECWCS ones i mentioned are tough as nails and what I use personally in the winter.
You will also want several pairs of wool socks, and several beanies/watch caps made of either wool, acrylic, or fleece, and you will also need at least two pairs of gloves. I also recommend a layered approach to gloves, a wool liner, a thicker fleece or wool glove, and a waterproof shell mitten.
Think in layers for everything, and in multipurpose items. You can always add or take off layers, but if you only have one super thick winter coat/shell that combines insulation and a waterproo barrier you will find yourself often too hot or too cold and sweating into it when doing outside chores.
So in summary you want to dress kind of like this, and can add or shed layers as neccesary to match the conditions.
Head: Balaclava, wool hat, the hood from your shell
Torso: wool baselayer l/s, wool sweater/fleece jacket, down jacket(hoodless is my preference), shell jacket
Legs: wool baselayer, shell pants, (some people like more warmth on the legs, if you find your legs get cold you can either get fleece pants, polypro pants, or even down pants to wear under the shell pants if needed. Fleece pants could double as good inside wear also)
Hands: wool liner glover, thicker wool or fleece glove/mitts, shell layer
For inside wear, those clothes need to either be multipurpose such as a fleece jacket and pants, or be limited to inside only.
A cheap way to get alot of these items is to go to local thrift stores. I buy alot of down vests, down jackets, fleece jackets/pants, baselayers, wool sweaters and long sleeve shirts for just a few bucks each. If on a tight budget and you cant find what you need at a thrift store, you may want to check our military surplus stores, the winter weight polypro baselayers are quite warm, comfortable, and usually a set can be had for less than $10.
Remember to think in layers, and different ways to use them. Example: Chopping wood, (i assume this will be done outside) You will get hot and sweaty because it is labor intensive. So you will probabl want your baselayers, and maybe a fleece jacket and probably not much else unless its snowing etc or brutally windy or cold. You want to avoid wearing your down jacket for example because it will get soaked with sweat and take forever to dry. Remember that things like wool and fleece will dry astronomically faster than down and also remain some of their warmth when wet or damp, whereas down when wet is pretty darn useless.
Sorry for the rambling, but hope some of this was useful. Feel free to ask as many questions as needed.