Some points which may help.
1. You can't go back to a previous role. So save the best ones till last. Don't promote anyone to Assassin unless (a) you are happy to lose this later on, or (b) you don't intend to promote her/him ever again.
2. Improving a high level role is very slow ( 13th level to 14th level takes forever) and gains only one spell and a couple of skill improvements, whereas changing to a new role then promoting up to your best level is very fast, and brings lots of skill and spell improvements.
3. By the time you have the opportunity to get a Zen Master or Valkyrie you are just about ready to face Cet in the final showdown anyway. Be prepared to either forget these roles, or to put the Cet Quest on hold while you sneak back to town.
4. Progress in spell schools is hard if the role doesn't support those schools. So converting from Priest to Monk is fine for Spirit magic, but puts a real brake on your Vine Spells.
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