I'm currently on Magento 1.8 and want to get to Magento 2.0
Would it be recommended I first upgrade 1.8 -> 1.9.? before attempting the 2.0 upgrade?
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From the various comments on my original question, and looking at the Magento documentation, it sounds like the best practice is to essentially build the new site from scratch on 2.0. Well, not exactly from scratch, Magento has tools to 'migrate' the data from older versions to 2.0. So effectively, you install Magento 2.0, migrate your data, and create new templates. From the docs it looks like it also supports incremental migration after you do your initial migration in case more transactions (new customers, orders, invoices, etc.) occur on your older site. This make sense since the initial migration can be very slow, but then updating just the new data can allow for a quick cut-over to the new version.
Much more information in the Magento 2.0 migration guide, found here.