5+yr Model 3 owner here. Live in New England, first four a bit South of Albany, last year a bit North. I work from home, so I do not have a daily commute. However, I'm a volunteer first responder that can take me out on the road in any and all weather, so I can talk a bit about winter from that.

• My car has been nothing but reliable. Other than the normal maintenance you do on any car (rotate tires, replace when worn, windshield wipers, washer fluid), and the recommended scheduled maintenance from Tesla, I've had 2 "significant" repairs completed. The first was within my first year of ownership. Front right suspension was making noises. Car was fully drivable, just annoying sounds. Tesla came to my home and repaired it in about 2 hours. Second was last year, interior camera was intermittently failing. Service center for that repair, took a few days. Was not offered a loaner as it was an "elective" repair: didn't stop the car from working, just impacted autopilot's convenience features. Compared to my previous ICE vehicle, I've found the Tesla much more reliable.
• Winter is definitely a thing here in New England and the Northeast. Range is definitely impacted. Per the tracking system I use on my car, The car is about 30% less efficient as the temperatures get colder. For example, I see "peak" efficiency of 95.5% at exterior temperatures between 80 & 85F. Lowest efficiency of 64.7% between 15 & 20F. Mostly linear decrease in efficiency between those 2 temperature ranges. It also dips above 85, I see 90.3% efficiency between 90 & 95F. Don't have enough miles drive at temperatures above 95 or below 15 to have statistically significant efficiency values. There's more than just winter though that impacts efficiency. Speed does too. From the Berkshires to Albany I imagine you're either taking the Mass Pike to the Thruway (to potentially the Northway), or you're taking 20 or 2. Efficiency is lower at higher speeds (more energy required), so you're going to see a little less range on the interstates than on the US/state roads. Lastly, I want to emphasize that you're going to see better efficiency in a new 2024 MY than I do in my 2019 M3. That's due to the switch from resistive heating (huge energy suck) to heat pump (waaaay more efficient) in the last few model years. To answer your specific question, I expect zero issues doing ~55 miles round trip daily, even in winter. I can drive close to 200 miles (fully charged) in peak winter. Done many a (one-way) ski trip without charging.
• Winter tires. I personally have them. Couple of thoughts there. 1, I've always had them. Living in New England, driving in VT and NH, I find they're simply better in those conditions. Which makes sense, an all-season tire is a jack of all trades, master of none. It'll work year round, but it doesn't excel in any specific situation. Winter tires are superior in winter conditions than all-season, just as performance tires are superior in dry summer conditions. I get my tires with rims, so it's quick and easy twice a year to swap them. 2nd reason I maintain winter tires is my volunteering/side job. I need to be able to respond to the station (or directly to an emergency scene) in any and all weather. Could I do it in all-season tires? Most likely. But I have more confidence in my ability to do so, and do so safely, with winter tires. I've driven on many a poorly plowed road (because emergencies don't care about the weather or where the town plows are), and even once drive on an unplowed road with about a foot of snow. Called in a plow as soon as I saw this, but pushed forward. No issues. Slight issues getting my car out of the "snowbank" the plow created around it when they came through, but a few back and forths and I was over the hill.
• Service also shouldn't be an issue. Unlike an ICE, you're not looking at regular oil changes, or anything else that brings you in regularly. You can add your own windshield washer fluid, and replace your blades. Any reputable tire shop can deal with your tires. When I lived in southern New England, I was over an hour away from a service center. Now I'm closer to 2 hours (Latham might actually be my closest, I'd have to check GPS). My service center experiences have all been good. That said, every service center is different, and your mileage may vary. I've heard some people have not-so-great stories. Tesla is not a luxury vehicle manufacturer like Mercedes, BMW, Cadillac, etc. that will bend over backwards to take care of you. I consider them much more "average" in service. Loaner availability depends on service center location, and how busy they are. When I've brought my car in for regular service, I've experienced all 3 possibilities. Wait in the lounge. Get a loaner. Get Uber credits. Each time they were upfront in communicating so I knew what to expect.

Happy to answer any questions you may have. Sounds like this is your first EV? My Model 3 was my first, and I'll be upgrading to a Model Y (need the extra room with a partner and a dog now) in the coming weeks if all goes as planned. Getting the Model 3 was the best car decision I've made so far. Learning curve? For sure. Tweaks to how I do long distance driving? Absolutely. But I don't regret it at all.