I regularly move my colonies around as I winter with all of them gathered together on a winter stand, which is not where the majority of them spend their summers. Summers many of them are spread around my farm.
I suggest reading what Michael Bush has to say about moving hives. He has some non-traditional ideas about moving hives that work quite well. I use a modified method which is based on his plan.
The major modification which I use, is that I no longer move hives box-by-box. I strap them together with four ratchet straps: two around the hive to keep it tight no matter what happens, and a second pair for the hoist itself. We use a chain with a large hook on the end that's wrapped around the bucket of our tractor to do the heavy lift. If I didn't have access to that, I would use a heavy duty handcart, extra straps to secure the cart and the hive together and some major muscle to move the cart. (I have a 3-deep monster at work that has to come into the fenced Apiary for the winter. We can't get the SkidSteer out to it, so I'll be doing the handcart trick.)
That's how the move happens. But it's not the only issue. Oriented bees are the second problem with short-distance moves. I lean heavily on Michael Bush's insights here, too. I always plan on having strong re-orientation prompts at the new location's entrance point. And I also use Bush's idea about a "Left-Behind" box for the first few evenings after the move to collect the slow-learners that fly back to the old location and can't figure out where they started from that morning.
To make this easier (and this part is different from the Bush technique) I install a triangle bee escape board on top of the hive on top of the uppermost box, or the upper vent shim if using one, and just under the telecover. I do this before the move so it's in place right from the start, without having to open the newly-moved hive to install it afterward.
The purpose of the escape board is to simplify the nightly re-joining of the main colony with the Left Behind box and its stragglers. The original Bush method called for setting it right against the entrance, but I found this awkward to do in the dark with the re-orientation prompts in place. I find it easier to simply remove the telecover and plop the L-B box right on top of the bee escape board (OK to do in the dark, the bees can't fly up at you with the board in place) and let them figure it out overnight.
The Left Behind box works like this: Late in the afternoon, or in very early evening on warm days, when the some of the bees are still flying, set it out on the old site. It's any box with frames, even undrawn ones, and no, or at least very little honey in order to avoid robbing) with an improved base and top. I like to have a strap around it so I can carry the whole shebang easily. Late-returning bees will find a box and take shelter in it even if it isn't their "home" hive. After dark, carry the box to the new location, unstrap it and set just the box - without base or top - on top of the escape board and under the telecover. The bees will stay in the L-B box while you do this if you are well-organized, quick, and gentle. I suppose you could leave the L-B top on it for simplicity and simply rotate the top from the hive back out for the next night's pick-up. I don't do that because my L-B tops are often just a piece of plastic, and not really tops.
The Left-Behind box should not be placed on the site until late in the day (or if the weather is going down badly, just before that happens) and it's only offered for a few days. Careful observation will tell you when you are no longer catching any clueless bees, and you can stop putting it out. I have only rarely had to do it more than 2 or 3 days in a row.
As for when to do the move: I would opt for doing the move in the evening (after dark, when all the bees are in) if you are moving using a tractor and the path is clear and smooth. This is a good time when you have to recruit friends to help. But I have also successfully done it early in the day before the bees have a chance to leave. I close them in just before dawn. And as for the time of year: I suggest doing it in warm enough weather so that issues of disturbing the cluster in weather when it's too cold for them to successfully re-establish it, and also when it is still warm enough for the bees to go to the old site, fail to find their hive and then still have warmth-enough and time to search for the new one before they perish from the cold.
One year I moved my bees on Dec 6th or 7th, right before a cool-down period. (I am in northern NY Z4b/5a.) As it happened that year the expected cool-down occurred, but then the Polar Express moved in right after that. The bees didn't leave the hive for nearly 6 weeks after the move (by their own choice because of the temps - they weren't penned in.) I was appalled to discover on the first warm day that thousands of them perished in the deep snow at the old site when they flew out. I had maintained the dense re-orientation prompts in front of the hive the whole time. So my recommendation to move them when it is still warm is based on that. Apparently, not withstanding the Received Wisdom of Beekeeping, it isn't simply time passing which extinguishes the bees' geographic picture of where they live, it is experience, too, discovering they are in the different or wrong place and re-orientating to the new one.
My final advice is repetitive, but worth being boring about: don't skimp on the straps. Two pairs of beefy ratchet straps per stack are not overkill. Two for the stack and two for the lift. And real ratchet straps, not wussy ones with just cams. I recently moved a hive that was under-strapped. When an attempt to lift it on to a tail-gate failed and the hived slipped backwards, it broke apart and I got dozens and dozens of stings from the outraged bees. It was the worst experience I have ever had with bees. And despite not having an "allergy" that much bee venom made me very sick, as it would for almost anyone. The bees would have been plenty-pissed by the drop alone, but the stack breaking apart allowed them all to weigh in with their fury. And, also, be sure to securely the close up the entrance before the move, even if a few bees are still loose. Better a few stragglers that need to be dealt with, than thousands of them taking exception to your plans.
If the tractor-bucket hoist idea is confusing, I can attach pictures that will make it clearer.
It will also earn you points if you decide on the site of the new stand, and prepare it now, even if you plan to delay the move until spring. My mother taught me that when supper is inevitably going to be late, the smartest thing to do is begin by setting the table. Evidence of progress goes a long way.
Nancy