To get straight to the point, usually a strata believe they can save money, or Bob needs a job in unit 304.  I am not convinced you will save money and or it is best situation for Bob to be cleaning in the building he lives in. (though I do agree Bob needs a Job)

Employees require a certain amount of administration to properly function i.e. who pays the WCB? Does he even have WCB? Does he have liability insurance? Who pays their other payroll deductions (CPP and EI)? What happens if Bob underperforms? How does building fire him? Deal with the severance? What if Bob is let go and he doesn’t like it? What will the strata do if he seeks compensation or damages, who pays the legal fees? How about if the decision goes against the building, who pays then? Or worse yet, In the event that Bob gets hurt does the building have a health and safety plan for WCB to review? What happens if he sues?

Did I scare you? Good.  What needs to happen is Bob needs to work for a professional cleaning company that will care for the administration.  This is what they do every day not to mention they will train him to be a high quality cleaner and provide him with the appropriate equipment and make sure he is using the right kind of cleaning products.