Hi Jowel,
Originally just the thought of collimating scared the proverbial out of me but I bought an Orion Cheshire collimator and read the very good Skywatcher manual and off I went. Patience and perseverance is the name of the game here. In very little time I found it easy and only takes me a few minutes (daytime of course).
I surpose that one factor of influence could be do you want the scope for visual or astrophotography. Visual is more forgiving.
Also, I would recomend forgeting about the locking screws as I found that they just warp the mirror out of collimation when they are tightened and that the scope doesnt need them anyhow.
As for how often, I have only collimated once in the past year and that includes three car trips! Just treat the scope gentlly and well padded in transport.
