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I automated searching for a rental property across all the major property websites in my country. In particular I was looking for properties with certain attributes (bathtub, lock up garage etc.), in a specific set of areas (GPS-based areas predefined on a Google Map based on proximity to train station, dog park, nearest shops etc. in suburbs my wife and I liked). None of the existing property websites offered anywhere near that level of search and notification customisation, so I cobbled together a Python script that scraped the websites on a daily basis and ran all the results through a filter. Anything interesting was emailed to us both so we could reply by email and have a conversation about it. My wife and I decided to be super fussy since we didn't need to bother manually searching. After about 6 months my script found a winner and we're now in an awesome place that ticks all of our boxes.

I didn't dare automate the application process... I had nightmares of 450 property managers calling me at once saying "Congratulations". :)

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