Answer to the question of whether we can sell one half of a property into the family trust in June and the other half in July seems to be yes, but with the advice to run it by our accountant first.
He also thought that selling half in June to the family trust and having the holding in the name of the private person and the family trust as "joint tenants" may be possible. It would postpone capital gains tax on the half held privately until the house was sold. He suggested we run this past our solicitor to check it from a legal stand point and also check the Trust Deed to ensure that it allows for the holding as "joint tenants".
Changing how the property is held from "tenants in common" to "joint tenants" was not advised because if one of the joint tenants passed away it would go to the other and in our circumstances, should the younger half owner pass away it goes to the older one, which is NOT what we want to happen due to other family issues. But in other families, and other circumstances this could be feasible, but because it does not help in our circumstances, this question was not really answered as to whether or not the ownership can be changed.
I hope this helps you PI141, and Terryw, I would be curious to hear what your thoughts and reply were. Until we run these things past the solicitor and accountant we will not know the answers, but it seems we can work things to our advantage and minimise the time involved in moving these two properties into the trust (fingers crossed).