Retire On One Property Deal goes some way to addressing such questions. I have known the author Barry Davies for a few years and can vouch for the fact that he has been downright, brutally honest about the pain and downsides of investing, ie when things go wrong, as well as about the huge upsides. Only by overcoming the former in many cases can we achieve the latter, and so it has been for Barry. The book starts with a painful personal tale of a deal that went horribly wrong and the fallout that went with it, then goes on to showcase how grit, determination and know-how can lead to a spectacular recovery.
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Retire On One Property Deal, Barry Davies
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This is probably a book that we should all read at least once during our lifetimes. Mentioned by Richard Brown, founder of The Property Voice, as one of his top five books in the Property Tribes Essential Book List, Man’s Search for Meaning is a classic in terms of understanding the bare essence of human nature. 
Another favourite of Nick Fox and included on the Property Tribes Essential Book List, How to Get Rich is a combination of business wisdom and wealth development.