Great questions. Let's try and address in order:
1. How are associates tracking? There are two ways of addressing. If you have companies that work with your property or management company they can provide CIO's (Certificate of Insurance). The resident should provide and depending on your PM Software you can track through this. A valid CIO should be required before the keys are given. As far as tracking this should be part of either your month end review for upcoming expirations if your software has it, reporting from insurance carriers your work with, or if neither a spreadsheet tracking. Having you listed as an "additional insured" should provide you with notification of changes in the policy or cancellation. There is always a chance of lapse from the time the policy is cancelled and you receiving notification.
2. How can you enforce? First, your lease or addendum has to have the language to provide this requirement including keeping in force during the term of the lease and any periods of "hold over." If you don't have the right language, you will have a hard time finding a magistrate or judge to enforce.
3. There are products and associations out there with companies that can do a lot of the work for you such as First Advantage Saferent and others offered as NAA Suppliers. There needs to be clear limits and requirements in your lease and addendum, which is the only way to provide for balanced program. Do not allow or make waivers in the established program, otherwise you set a precident that will jeopordize your program and legal basis.
4. YOu never are selling insurance unless you are licensed in that state. Any affiliation with the companies working with NAA will tell you how to present, and your staff should never state anything that would lead to the perception this is what you are doing. Here again, legal terms and training of your staff is critical.
Hope this helps