It appears that headroom was tight when that milling machine went into place in the building- one of the joists in the ceiling looks to be notched to allow the big multiple=vee belt pulley to clear. The multi=vee belt pulley has almost a solid web, and is a flywheel as well, so plenty of weight there. My suggestion is to take the drive apart in place, since lowering it as a unit does not appear possible.
A trick I've used in low-headroom situations like the one pictured, for raising or lowering lighter loads, is to drill holes in the joists and pass a piece of round stock or a piece of pipe thru the holes. The holes need to be drilled (or hole-sawed) on the centerline of the joists. This is known, in engineering, as the "neutral axis", and is the point at which there is zero bending stress. A hole drilled or hole-sawed a bit larger than the bar or pipe will let a longer bar or pipe be angled and slipped in to span the joists. A rope can be snubbed around this bar or pipe to let things down, or a light chainfall or comealong rigged off it. Without knowing the framing of the building, I would not go more than 250-300 lbs on this sort of rigging. Letting down the countershaft with the cone pulley, flywheel/pulley and pillow blocks will get rid of a lot of top-heavy weight, as will removing the motor.
Once the drive is removed, the center of gravity of the mill moves down towards the base. As has been noted, getting the mill on skids is the safe way to go about moving it. I use rough-cut 4 x 4s or 6 x 6s from local sawmills. I bring my chainsaw for jobs like this one, and cut the skid timbers to length. I also cut the ends of the skid timbers on 45 degree angles. This makes "sled runners", and makes the job of moving the machine on rollers or simply dragging it up the ramp of a trailer a whole lot easier and much more stable. I use lag screws and washers to secure machine tool bases to skid timbers, when I cannot use carriage bolts. I have an electric impact wrench which works wonders for driving lag screws. The building floor in your photos looks like a dirt floor. Some planks and pieces of plywood to make a
"runway" to move the mill out on using pipe rollers is how I'd go about it. I'd bring a pick and shovel to level off the dirt floor as needed, and some smaller pieces of plywood or 4/4" board lumber to use as shims to level off the plank or plywood runway. A machine tool on skids, moved on pipe (or solid bar) rollers, moves quite easily. It can be steered and moved along with a pinch bar and by angling the rollers, the machine tool will turn on a dime. The rest of the story is that the runway planks or plywood has to be fairly level and well supported. If there are any divots or dips, the machine on rollers can behave like a hog on ice when the weight comes on the rollers that find the soft spot or dip.
I use a 1 1/2 ton chain comealong for this sort of move, and coming up the ramp of a trailer, use a second comealong as a "safety" to keep the machine from toppling backwards off the ramp. I tie the second comealong up high on the machine being moved and run a chain or sling to the trailer tongue. The comealong doing the dragging of the machine up the ramp is set low, with a sling made up around the base, just above the floor mounting flange. As the machine tool starts up the trailer ramp, there may be a tendency for it to want to tip backwards down the ramp, and this is where the "safety" comealong made up onto the top of the machine tool comes into use.
I also try to avoid using any rollers for the move up the ramp, as having a machine tool get away on a ramp is something that is quite dangerous.
My other caution is to avoid getting yourself between the machine tool and walls where you might get pinched or squashed if the machine shifted on its rollers or hit a soft spot in the dirt floor. If you see the machine is starting to topple or fall during the move, get away from it as fast and as far as you can. You are physically incapable of stopping a toppling milling machine and to try might get you seriously injured or killed outright. It's not worth it. A little extra care up front on rigging jobs is well worth the added time and expense. Skids increase the footprint and add a lot of stability, and lowering the center of gravity by removing the drive will help immensely in making the move go a lot more easily. Good rigging- slings of known load rating or good chains- and good working comealongs are a necessity. Trying to rig with half assed light cable comealongs and rope can be done, but it is more of a chancy proposition.
Where in the Hudson Valley are you located ?