A few pointers: in cold weather, it is actually easier and warmer for everyone if baby is worn directly against you, with a coat or sweater (or both on really cold chilly days!) around both of you. I did NOT have a snowsuit for my two youngest when they were babies, as they were always worn on me. They eventually got snowsuits for playing outside in the snow once they were 18 months old or so. I can happily say it saved a lot of time and hassle in wrestling them in and out of those things. Not to mention the fact that the baby would not overheat, since I could quickly whip off the coat from both of us when entering stores.
This is exactly what I do in cold weather when I am not carrying her in the (warmer) carseat that has the warm wool cover that zips up. I put the sling on, set baby up in it in front, then put my coat on. Baby has her little hooded cape on hanging over the rail of the sling, and then I just hold my coat as closed as I can. It's not big enough to zip up around the two of us, so I don't bother trying.
Hi OP, I also live around Boston. And have done lots of baby wearing in all sorts of weather. DS was born in April & it was really warm the following summer, but we still walked A LOT ... sometimes miles at a time. Uncomfortable at times? Yes. But also totally doable. I think I was more uncomfortable than he was too as he would usually just sleep & sleep. Planning our clothing was the most important piece. (And I was also using a moby wrap which I would not suggest in the humid summer... a woven wrap would be much better).
And I'll just add that strollers are the biggest PITA on the T & buses! Baby wearing on the public transportation around Boston is so much better.
As for how to lug your stuff. I found a regular ole' backpack works just fine. But a side satchel has been my favorite -- much easier to get into if I need something while still wearing DS or as a way to balance (sling on one side, bag on the other). I also just started using a cart for groceries. Very useful.
Hmm. Bike path is awesome & there are many low-traffic arteries that are safe with a bike + kid. You should check out this blog for inspiration. We waited until DS was 1 year, so you have some time yet! Also, we opted for a trailer so that we could easily hitch it to both bikes & lug groceries etc (which is just about impossible with a regular bike seat). But each has its pros & cons.
Oh, also wanted to mention that there are usually great, cheap strollers on craigslist, should you find that one would be useful for you at some point. I found a lightweight graco in great condition on there when my back started hurting & I was unable to carry little guy around all the time.
I googled up this group. I know there to be other MA. groups as well. I would suggest you go and talk to those who are experienced with your local area. See what they are using and how they use their stuff. This might be the best use of your money and time. :O)
We also share a car and whoever is at work often has the car, so that leaves the at-home parent with many hours to fill going places on foot. I find, personally, that the ring sling is wonderful for newborns. I had dd in it days after birth and she practically lived in it (and was worn to sleep in it) for the first 3 months. I likes the adjustability of it and the fact that I could wear her to sleep and then pass the whole sling, with baby still in it, to daddy to give me a break, or just lay her on the bed and ease her out of it gently.
I also have a wrap (well, actually its just several yards of remnant fabric haha) and once they have head control it's a freaking lifesaver. Put it on snug and tight and I can go HOURS in that thing with no discomfort whatsoever....after a couple hours the ring sling tends to wear on my back a bit. I've gone all over the place in that and I prefer it to the stroller for several reasons.....in bad weather I feel it offers more protection. Baby's torso and upper legs are covered by the wrap. I will tie a jacket or blanket around my waist to cover her legs and feet if it's raining heavily. I put my own jacket on over the baby and myself, and put the hood over her head. Then I pop open an umbrella and we're good to go. I walked about 4 miles like this once during a torrential rain.....DP, ds and myself were all soaked when we got home but dd was dry as a bone! In a stroller she would have been cold/wet and subject to the wind.
Strollers are nice for places like amusement parks and maybe the mall (although we babywear there too, or just rent a shopping cart with a seat). But we don't currently own a stroller and when we did have them (we had an umbrella stroller and a sit n stand) we didn't use them. I think the sit n stand got used 3 or 4 times, total and 2 of those times were for ds' amiusement because he thought it was a riding toy.
I never use my stroller. Got it for ds1, used it twice, and it's been in the garage since. We do own a car though. I just always make sure I have 2 carriers on me.
I used an stroller with my oldest for the first 6 mo, After that we give away our stroller, have another baby that never been seating in a stroller. Although we're not car free ad live in area with terrible public transportation and semi rural. My only tip to ad if a good sun hat for you and you little one, and a nice gaze wrap for very hot days.Also, I second the idea of the waist pouch, we ECed and used to just carry my wallet, cell and a diaper/pant.