Thanks guys. Let me see if I can provide a clearer picture of what I'm working with. The house is over 100 years old--a brick row house in the center of a block. Most walls and all the ceilings on the third floor are plaster, with lots of lumps and bumps and a few small cracks, but mostly solid. There are no ceiling moldings. To call what is above this floor an attic is a an exaggeration. It is a space that ranges from about 3 foot tall at the front of the house to about half that at the back of the house (roughly 40-feet on that floor...first and second floors have a bigger footprint and do not need insulating between living space and roof.) There is a central air (newish high-velocity, narrow tube) system that snakes around the "attic". The blower is installed at the one access point there had been. This system serves ONLY the third floor and has two outlets in each of three small bedrooms and one in the tiny bathroom. The system serving the first and second floors is in a second floor closet. The insulation guys tell me that they can blow insulation in but will need to cut at least one new mansized hole in the ceiling to get in--possibly two, one toward either end. There are no recessed lights on the floor, and only three overhead lights at all. All other lights are wall brackets, wired from the floor up, rather than from the ceiling down. Of the three overheads..one was put in new by me, so isn't K&T. One the previous owner says was moved by them, so isn't K&T (But may connect in to K&T at the meeting of wall and ceiling. And one is the bathroom overhead, which can easily be checked. My electrician replaced the fixture there, so he should know what's above it. The roof is asphalt and fairly new (say 5 years old?) so, I'm not inclined to want to replace it anytime soon. I've gotten a quote for $950 to cut an access whole and blow in insulation. I'd have to pay someone else separately to fix up the access panel afterwards, probably adding another few hundred. Most neighbors don't even try to do much of anything with ventilation in their "attics", as they are all scared witless of cutting holes in their roofs. But I have found info on the Brooklyn Brownstoner blog about successful attic and whole house fan installations and one neighbor loves the whole house fan he has which sits in a sort of plastic cove on the roof. Unfortunately, he bought it with the house and has no idea who installed it. I don't intend to move in the near future, or even the more distant future. But I would like to make the third floor more habitable in the summer, especially since at some point in the next two years or so, I'd like to turn it into a separate apartment and rent it. Honestly, I seem to be finding such conflicting information and I'm so dubious about how knowledgeable folks you hire to do this stuff are about old and "out of the norm" houses that I really, really, do appreciate any and all help I can get here on this forum. Thanks,

My best suggestion is that you figure out your priorities. You may want great insulation and a durable roof that looks good, and you may want it all for cheap. You probably won't get all of this. If you don't prioritize then you won't know where to compromise, and you'll keep going in circles. Also, try and find a professional to work with who actually understands the way your roof is supposed to work, or else you'll just be throwing money away. For example, if your roof is ventilated then any insulation you put on top of the existing sheathing will be pretty much useless. You probably need a smart general contractor, not a roofing company.

You need to fir out the interior and create a stud wall around the entire perimeter. You also need insulation below the floor, and at the ceiling line. The stud wall will give you room to run the required electrical and attach drywall. You will also need to update your windows in any bedroom to those that permit emergency escape. You also need a plan for the rough plumbing creation, which in your location will easily freeze. Which is why many homes have basements. And all of that presumes that the building has an approved foundation type for a residence, and the local municipality will permit its reassignment from agricultural to residential. The typical pole barn foundation into dirt is not approved for a residence. A pier and beam foundation would, if the piers are concrete and below the frost line. But that causes many more issues with the needed insulation and plumbing in your location. It's unlikely that the building could be as cheaply converted to a residential classification as a new build designed to fulfill those requirements be built correctly from the beginning. Retrofitting is always much more expensive. Especially without a proper foundation.

That's a LOT of stone on the front facade. I'd keep it to the garage and post bases, only, then do stucco for everywhere else stone is called for. I think I'd go for a dark green roof, keep the trusses the same color as shown, do a sage/gray color for the shakes, and find stone that will work with those colors. Keep the garage door, the front door, and the front posts the same stain color as the trusses. The shakes and stucco should be the same color. This picture is similar to what I had in mind, but I'd go with a lighter stain color (still too much stone, IMO): Here's another option with a sagier green: