This paper addresses the three somewhat disparate issues listed in the title. The first section of the paper surveys the common law rules (throughout Canada) and statutory rules of several jurisdictions within Canada (at the time of publication) regulating the duties of a landlord and tenant to maintain and repair certain parts of leased property (and associated properties, such as elevators, hallways, parking stalls, etc.). Issues that must be addressed when considering these rules are listed at the end of this section. The second section of this paper deals with security or “damage” deposits. Although it is a general rule that individuals may contract with each other however they wish, there are many statutory rules that govern these types of deposits. The section reviews the statutes as they stood at the time of publication in various jurisdictions in Canada, makes some general observations on the nature of these deposits (and the opinions of different interested parties on them), and addresses issues related to these deposits. The final section of this paper addresses regulations that govern the practice of requiring tenants to provide post-dated cheques to cover future payment of rent. The paper discusses the rules existing at the time of publication in various jurisdictions throughout Canada, as well as the issues related to this practice.