For starters, if you want to keep the itching and swearing to a minimum - just go and buy the right size hole saw from Trade tools or Bunnings or where ever.
The number of six packs required will purely revolve around your personal tolerance to alcohol coupled with your ability to manage rapidly spinning power tools that have the potential to not only do untold damage to nice shiny gelcoat but also remove parts of your anatomy to which you may (or may not ?????) not only be attached to but fond of. Not to mention the increased chances of getting your new toy the wrong way round in the hole - don't laugh - seen it done. The things are a lot easier to get right the first time than remove - trust me on this.
The side of the hull thing makes no difference mechanically with the transducer mounting. Provided the arrow points to the keel it will work on either side of the hull. The reason Airmar say the starboard side is that with a standard rotation propeller, that is the side that the prop is forcing water away from the hull and is in theory least likely to create interference. I have installed many transducers over the years on the port ide of hulls and they have worked fine but you won't know for sure until the thing is in just whether there will be any issues - this is the unfortunate side of thru hulls.
I have a zero degree thru hull in the Victory that is mounted in a planning/Lifting strake - the thing Airmar say to avoid, that works fine. There are no hard and fast rules. Personally I would be trying to get a bit of space between the prop and the transducer anyway - ie - mount it a bit further forward if at all possible. As such the side of the hull should be less critical than when the transducer is in close proximity to the prop. Make sure that you have no strakes that finish half way down the hull or other fittings from toilets etc. in front of your location and your chosen location will not cause rollers to contact the transducer face during launch and retrieve. Measure twice, including the cable required - drill once ( it's cheaper that way)