You are right, positioning is a little bit tricky.
Some software allows to merge different designs in one hooping- this might work for a word like "HIS" but not for "Happy Christmas", for it is to long.
I think the best way is to print out paper templates of the designs, arrange them on the fabric and then mark the centerpoints and the outer guidelines of each one.
First link is for merging.
Second is (one of many) for multi hooping.