To sort of just recap what others have said

• Option One: Driving all the way in - you obviously need a car for this, it's likely (not guaranteed though if traffic is gnarly) your most direct/fastest option but also possibly the most frustrating. You also have the most immediate access to your car which is nice if you need to leave early or late. For parking, I agree with others that if you're parking in the city, find a garage or lot on something like SpotHero and have it ready - it's not insane to park in the city most of the time but it's likely worth the money to just pay to do it. The biggest frustration might be getting to the parking
• Option Two: Driving into a T Station of some sort - it likely depends on where your meeting is as to what station but either Alewife (Red Line) or Sullivan/Assembly/Wellington/Oak Grove (Orange Line) are usually available and you can use the T to connect to nearly anywhere else you have to with a short-moderate walk. The upside of this is you cut out the worst driving (inside and just outside of Boston) and parking/T costs will likely be cheaper than the gas/parking of going into Boston. The downside is you need to budget public transportation and walking time and, if your meeting place is out of the way, it may be a substantial amount of time. Additionally, if you are staying later into the night, the train frequency slows down a lot and stops earlier than other cities do, so you may be stuck getting an expensive Uber to get back to your car - your car also needs a T ride to get back regardless.
• Option 2.5: Driving to a Commuter Rail Station - same concept as the above really and you can get in from slightly further out, but you're taking an additional train on weird schedules.
• Option Three: Taking a bus - likely the Boston Express or Concord Coach - to South Station and use the T from there. Bus tickets vary from location but if you're picking it up in NH (likely in Derry/Londonderry for instance) it'd be $20ish each way and at set times. The upside is that you're doing no driving in Mass and it's really no slower than driving into Boston. The downside is you are really subject to the bus schedule - as it goes into the evening they become very infrequent with a potential two hour gap near the end - and if you miss that you are stuck except for a very expensive Uber ride all the way back to NH (eek).

Really, all of this is very dependent on the nature of your meeting, flexibility requirement for time, and overall tolerance. There's no perfect answer - my personal preference for going into Boston is #2 but any of those are defensible depending on the situation. Plan it out for sure.

Prep for the downvotes - I do recommend searching the forum history, especially in the last two years and change NH has become a very popular place to move to. The housing market, much as it is everywhere but maybe even more here, is very difficult. Lots of demand with money from South (like Mass, CT, etc.) combined with a lot of attractive factors within the state (the fabled close to everything element). I saw with other posts you're looking at VT too so I am guessing it's more of a location thing as opposed to political thing, so I'll try and angle it that way. This is all my opinion

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Best Things

• The "close to everything" element is quite real. Just taking from South-Central NH (where most folks live), you're within probably 1.5-2 hours of the beach, mountains, hiking, and a major U.S. city. I'd argue this also extends to amenities - for the most part you'll have reasonable "by car" access to most things and commodities you may want.
• Similarly, depending on what you want - provided you have money - you can get the living experience you want. Like, in NH there's absolutely places with real acreage in a woodsy area that is within 10-20 minutes of retail and restaurants - many at that.
• The seasons - it's a cliche but a real one that you do get some elements of all four seasons here. I can't say I love the extremes at all (more on this later) but if you are a person who likes the outdoors you get a ton of variability here.
• The people are generally aight. Like, the most combative NH residents I've met are here and you can block them easy enough. People aren't gonna drown you in niceness and it'll vary by area but it's pretty nice if you generally want to be left alone. Obviously big YMMV there.

Challenges

• Costs. It's expensive and there's not exactly many shortcuts. I mentioned the housing market before and it's very tough to find a good property or rental in a good area as is, but even when it's not living frugally here is very tough. I'd argue state wages generally haven't kept up with cost of living and there's a reason a lot of people do an absolute trash commute to make it work. If your range is 850-900k this may not be nearly as much of an issue for you. The market is softening a bit too.
• The seasons - the issue with four seasons is that we're not really built for heat IMO as an overall area. It can be downright unpleasant for weeks on end and the infrastructure/relief will likely fall on you to account for. Likewise, winter can be a massive pain. We prep well for it up here but if you don't like cold/snow it sucks and even if you do, you have to spend to mitigate it or work to mitigate it.
• You need a car...maybe two for two people. Even in a city. Just not much in terms of public transport
• Generally, I think culture is lacking. Like, NH has some good live performance venues and minor league sports but most of the time the best musicians, performers, etc. will skip over NH for Mass/VT/ME - especially if it's not the summer. This bothers some more than others but it's a grind if that's part of what makes life worth it.
• Utilities - eh. Electric is expensive, heat's expensive, raw materials are expensive, choices suck, cable sucks, etc.
• Big lack of diversity. Not just racial but also experience based, education based, etc. That's a subjective con but I think we're worse off for it.

In terms of places to live, if you're honestly looking 800k-900k the state is your oyster and probably depends, in my view, on what you want to do in the state. Like at that price I think you can live anywhere in the state, but it you're gonna get a lot more house/land for your money the farther north and farther west you go - but if the importance is access to something, it may be worth taking less to get closer. If I were doing this I'd be looking in adjacent towns to the big population centers and going out from there, but if you don't care about being close to a Portsmouth or Manchester, you'll get a ton more landwise not doing that and relying on the shops/stores in smaller localities - except the Lakes/Resort areas, that's a different monster.

I’ll echo Grappone. The other dealers I went to ranged from pretty good to disasters but the only iffy parts of Grappone were the trade in value for me and add on run through and neither were that bad. I’d go back.