I work on the tech support team at Intercad (The largest Australasian VAR). I hope I can provide some unbiased feedback on your questions to help you make your decision...
1) The RRP is somewhere around $12,000 AUD for SolidWorks Standard not including the annual subscription fee. This price fluctuates depending on the exchange rate and any discounts the reseller may offer you. Unfortunately there really isn't any other offerings from SolidWorks with the exception of student/research licenses that may suit you.
2) It is a breach of the EULA to purchase and use a license from outside your country. You need to purchase locally (within Australia) to be compliant. If you do purchase a license overseas and move to Australia, you are required to fill out a form that indicates this and will assign you a new reseller, even if you do not have a current subscription. There is a fee associated with this and a new serial gets created for you.
3) It is mandatory to pay the first years subscription and is a requirement placed on the reseller by SolidWorks. This is what we refer to as 'onboarding' where we expect you to place a higher strain on support to learn to use the software and offer assistance accordingly. Remember that during your first year of subscription you will always be entitled to the next version of the software as well as the current version when you first buy. So your subscription pays for this up front. You will have also paid for support up front so you can use this as much as you need.
Thanks Logan for your detailed input. I shall wait for more inputs from varied sources here before reaching a decision on the direction to take.
More varied inputs? Who is better to answer your question than an employee of a company that is authorized to sell you a license?
The only other legal avenue I have heard of is to purchase an entire company that owns SolidWorks licenses. Note that you can't buy "used" licenses from another company, you must purchase the entire company and its assets. This sounds crazy, but if you can find a small design firm with one seat of SW that wants to go out of business then you may be able to purchase it. If you want to stay up to date with versions and service packs you will, of course, have to sign on to subscription with a VAR. Of course, I'm not an attorney, plus I don't live in Australia, so please take any of this as worth what you paid for it.