Self Managing STR at a distance

[Simone Koga]

I'm in escrow on a property in Maui that we'll be using as a vacation rental.  We were originally planning on going with a property manager at 20% just because of the ease.  The more and more I think about it however, I would really like to try and self manage at a distance (Bay Area).    I'm putting together a list of roles I would need filled, cleaners, on-island contact, handyperson, etc. but I want to be as thorough as possible.

Anyone finding success managing a STR from afar? Wha are your tips/tricks, must-haves and nuggets of wisdom?