For the majority of people, working makes no difference to their likelihood of gaining employment. If anything it works the other way around - once people have permanent settled accommodation they can begin looking at moving into employment, not the other way around.
Whether people feel 'entitled' or not is irrelevant, they are not entitled to accommodation whether they work or not. Being unemployed immediately removes the possibility of buying and without a legitimate reason for being unemployed i.e. disabled, elderly etc. they will not be entitled to any assistance from the local authority, be that in the form of homelessness relief or council housing.
Stop believing in this stupid concept of a 'dependency culture'. What dependency? What culture?