Thank you so much for answering the questions and it helped to give me insight into how things work with your boss.
The reason people get away with the kind of behavior that you have described is because they can and have. As long as there is a payoff for negative behavior, it will continue. When the rewards are no longer present then, and only then, will this unacceptable behavior change.
If this guy continues to goof off, you need to take it to your boss IMHO. It is important that you go armed with the facts, not just an accusation that he is not doing his job, but exactly how it is affecting you and the tenants of the complex.
When you are making rounds and you see areas that have not been cleaned you may want to take some pictures and make sure you note the dates and times the pictures were taken. Also document what the tenants are telling you but just their comments, date and time. Do not include how you feel emotionally.
Remember to be assertive and not aggressive. I hope you soon take steps in talking with your boss. This "guy" is being paid to do his job and therefore he should be doing it.
All of the above are great ideas. Especially taking pictures and maybe doing some personal follow-up on complaints. Your job is to keep the tenants happy, right? I would sit down and talk to the owners, with documented back-up, and set some boundries for acceptable and unacceptable behavior from your maintenance crew. I know it is stressful and this causes anxiety. Just keep working on solutions and you will get there!