There is a wonderful way of moving sheep one at a time, which causes great amusement to passing townies, and just confirms their perception of countryfolk as
sheepsh@??£3$.
One person straddles the shoulders of the sheep and holds it under the chin whilst the other person shoves from behind. That would be one way of moving your ewes, one at a time.
Or you could try halter training them as you go - they should have the idea by the time you get there and it will be useful for next time.
Have they been in that field before? If so, then they may well be happy to lead the way and just walk - maybe you could rope a friend in to open the gate at the last minute. It might work to put some food down for the sheep already in the field to distract them from the open gate.
Another possibility if they will follow a bucket is for one of you to lead with the bucket of food, whilst the other follows to mop up stragglers.
We used to walk our sheep across and along the road, but our traffic is fast so we had to get a couple of neighbours to do traffic control. We would put hurdles right across the road to direct the sheep, but I have a sneaky feeling that is possibly not legal. Once they had done that a couple of times they knew where they were going and would flee and fly across at top speed.
Now we load them into the trailer and tow them.
It sounds as if the ram just needs a normal hoof trim to cut back the overgrown bit, but it's as well to have purple spray there in case there is more of a problem than you think.
To separate out one animal, we would put a spare hurdle across one corner of the catching pen (tied securely top and bottom) so that animal would be safely confined while we concentrated on the others.
You will eventually work out a system which suits you, your land and your animals.