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Anytime you want, but definitely before you buy an investment property! In fact, don't just calculate it once, calculate it multiple times to ensure there are no mistakes. Initially you can calculate it just to give you an idea as to whether or not you should pursue a particular property, but once you decide on a property, spend more time really digging into the numbers and ensuring you are being as accurate as possible in your calculations.
There is no right answer to this question except, 'a positive one'. In general, your return should in fact be positive but it should also be positive enough so there is room for error. Don't settle for a positive cash flow of $50/month because that doesn't leave any room for any unforeseen circumstances (of which there usually are in real estate). Different markets and different property types will warrant different ROIs. You are best to understand the full picture of what you are buying in order to determine if the ROI is a good one or not.
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