I'm having to buy a lot of equipment, because I haven't really done any serious cold weather hiking in ages. (Mostly because there isn't any serious cold weather in the deep south). We are planning to start in early March, so I know it will be cold. I don't really like to be cold. But I need to remember, it's not going to be like the cold of my childhood in the frozen badlands of eastern Montana. It's going to be cold, but if it is *too* cold we can always get off the trail for a night or two. I don't need to prepare for 40 below temps.
I ended up buying the Mountain Hardwear Ultralamina 15 degree bag, which is a synthetic bag. I don't want to be cold, but I especially don't want to be wet AND cold. (Down bags lose their insulating properties when they get wet). I have a silk liner I'll use inside the bag, which should add another 5-10 degrees of comfort. I also purchased the MSR Hubba Tent, which is a 3lb 4oz single man tent. It got a lot of great reviews, and I like it because I can sit up in it without bumping the top of my head. It's a little tighter than I'm used to (2 man tents have plenty of room for 1 person!) - but I'll get used to it. I set it up in the living room - laid in it for a while - this shit's getting real, yo. Discovered that Emo the Cat will not make a good hiking companion - he was far more concerned about the tent taking up his sunbeam space than he was in doing any exploration.
I got a lot of stuff from backcountry during their 50% off sale items - couple different jackets to try out, variations on long underwear, socks, etc. I found a synthetic insulating jacket I really liked, and some smartwool midweight bottoms that are super comfortable. I'm trying to buy things on sale, and not buy shiny things just because I can (I have a 10 year old MSR stove & a titanium pot + lid + holder that is super light). That 1k max I was planning to spend is basically blown with the tent + bag + shoes + backpack. So if there is something I already have, I'm going to try to use it. If it breaks, or if it's not working as it should be, I can replace it on the trail.
I did score a nice under armour sleeveless tshirt for $2 at the thrift store this weekend. I tried to find a funny trucker hat to wear but couldn't find one that fit. Maybe next weekend.
E. and I have been going for walks on the weekend at various state parks in the area. Last weekend I just wore a daypack, and yesterday I wore my old pack - "squeaky" - loaded with 25 lbs. Not bad. Next weekend I'm going to rent a pack from an outdoor store, load it up with all my stuff, and go for another walk. I really like being outdoors, so I'm having a lot of fun. I'm not really sure how to prepare for the mental aspects of being on the trail - being away from E. will be the hardest part of it, I think, and I know I'll go through my own "Appalachian Trials". Just gotta be ready to face them.