I couldn't quite follow your post (probably because it's late at night and I can't think straight) but it looks like you're breaking the first rule of Calibre:
Use the built-in columns for what they were meant for.
Don't store series information in the title column. Store the title information in the title column, and the series information in the series column.
Take it from someone who's made all the mistakes and learned the hard way that there's a reason for the way Calibre organizes things. In this case, there's a very simple reason: It's easier to merge fields than to split them.
If a field holds exactly one piece of data, you can use templates and plugboards to combine it with another field that holds exactly one piece of data. But trying to extract one piece of data from a field that holds two pieces of data is far more difficult. For instance, what if you want to look up a book and you can remember its title but not its author or series?
Go ahead and use your MyTitle column to store both the series and the title in one field if you want. You can even set up a custom column template to do the merging automatically. But take the series out of the built-in title field.
Do this, and you will thank me one day.