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I guess I want to know from the seasoned investors here is if this strategy is comfortably achievable as it will be my worst case scenario

Well, roughish plan is to retire in my 40s (20 odd years time) and live off rent. To achieve this the lazy mans way was thinking of just purchasing a house every few years over 20 years then sell some down to reduce debt and retire off rents. Not looking for much, maybe circa $1,000 pw after tax...