You are talking about moving from one system to another. This means you will be switching rabbis, at least slowly. For the particulars you will have a rabbi, but as for your destination, you will be going on your own until you land.
Very often your current rabbi will recognise a sincere desire to move on and he will encourage you, and can give you guidance until you lock in to the next tower. This is obviously not always the case, though. Perhaps you should reach out to someone from your destination Hashkafa as a guide for rate of climb/descent.