To sell or not to sell, that is the question.  Or at least it is when you’re thinking about what to do with your investment properties after you move into a retirement community.

First off, let’s start by saying that moving into any kind of senior community doesn't necessarily mean giving up all of your other properties, but it can get complicated. If you own a vacation home in a favorite destination you can still enjoy visiting or make an investment property continue to work for financial gain. If you're being urged to sell, but just not ready to part, consider these thoughts in our guide to retirement living before making your final decision.

1. Can you afford to put your vacation property on auto-pilot with property management specialists?

Can you afford to hire a property management company for property that you cannot oversee yourself? If the property is in a prime location, a specialist should be able to negotiate a rate that covers both basic upkeep fees and any other potential maintenance—a particularly important factor whether your home is on a lake in the Midwest or on a beach in Florida. When weighing the pros and cons, consider the location. If the home is paid off and will sit closed all winter long, then maybe it's not a financial issue, but if you still have a mortgage and the property can only be accessed part of the year, that may motivate you to consider selling.

You’ll need to have a separate conversation with your children if it is a property that you want to keep in the family. If your children don't show an interest in maintaining the property when you no longer have the energy to manage it, however, you must decide what should be done with it at that point.

2. What expenses are associated with non-vacation income real estate and property?

This decision depends on similar factors to vacation properties, but not all income properties actually have a building or house on the grounds. If you own property in a prime location that only has value because of where it's situated, weigh the factors carefully.

Is there a large enough offset where you're making enough money to cover financial advisement/supervision fees? If so, keeping this in your investment portfolio will likely take little to no work on your part.

If you decide to keep a property as an investment and allow renters to live in the property, how much of the maintenance responsibilities will your property management company accept? You’re not going to be able to run out in the middle of the night when your tenant calls you about a leaky faucet—and unless you’ve already cultivated a relationship with service companies in the area, it would probably be difficult to find a reliable plumber if your don’t live in the same state.

You'll most likely need to hire a full service company that manages every aspect from screening and rent collection to indoor and outdoor maintenance and landscaping. You will even need to discuss if the property management company can help you manage property taxes or if this is something your financial supervisor or accountant will communicate about on your behalf.

If you live out of state, be sure to spell out all details such as 'only call if there is a dire emergency with property' or 'please contact my children at this number in case of emergency and me if they cannot be reached.' You might as well be managing the property yourself if the company calls you several times a week with questions.

To truly enjoy the retirement lifestyle you have envisioned, first be sure your property investments make sound financial sense.

Keeping a property solely for sentimental value may not be the best decision—for you or the children you wish to inherit the property. If keeping your other properties means you still get to personally enjoy them or reap the financial rewards, it may be a great decision after giving it this thought.