A swimming pool is a very attractive feature to have in your rental. Unfortunately, it attracts families with young children that are more likely to have an accident and/or drown.
First and foremost you need to know your tenant very well before handing over repairs to them. Some may save you money, but others may end up costing you more in the long run. Maybe your tenant is a trustworthy, hardworking, divorced father that pays his rent on time and is handy and/or employed in a maintenance position. This would be a no brainer, and could be a good thing for both of you.
However, another type of tenant may end up costing you more money, if they don’t know how to fix things they say they can fix. They may not care about doing a good job, or they may say they will make the repairs but never do it.
Many landlords choose to rent to family and friends and then others decide against it. Whether you do or not is completely up to you. However, there are advantages to renting to family and friends.