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Welcome to IceInSpace! You are going to enjoy this Peter. Seems to me that equipment and capabilities have moved on significantly over the years so your money will get a very respectable performance.
First things first. You are in Melbourne. Where do you think you will do most of your observing - suburban backyard, or take it all and drive away from Melbourne for an hour to get to darker skies? Where are you with respect to the city and its huge skyglow? Moon, planets and brighter stars are no problem from most suburban areas, but nebula, galaxies, globular clusters etc. are much more challenging and require the biggest aperture you can afford, especially if you are competing with city skyglow. Some filters can assist.
Are you happy to push/pull your scope to follow planets as the earth rotates beneath you feet? Or would you rather have the scope driven by motor to keep the object in your view? For higher magnification observation of the Moon, Jupiter and Saturn, motor driven is best. With a limited budget, you will trade off aperture for motor drives (and the EQ mount that is the basis of these particular motor drives).
You may find the approach is to go with a particular approach now, leaving an upgrade path for later - eg. get the biggest aperture on a hand operated EQ mount, and buy the optional RA motor drive later when you can.
Are you happy to search for the objects yourself and point the scope at them, or do you need some form of computerised help to point the scope at the object? For Moon, Jupiter and Saturn, it's easy to do manually. Fainter objects can be more challenging to locate by hand.
Re "squinting", there are a few solutions. One, as you mention, is choice of eyepiece. We can come back to that in future. Second is not to squint, but to keep the non-observing eye open. In a location that is not really dark, this can be distracting, but a cheap eyepatch from the Pharmacy and you can keep both eyes open easily.
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