There are many people that have the means who own two homes. In some cases, they may own a home as their principal residence in a tax advantageous state. The savings in state income taxes alone if they live in a no income tax state could very well pay for the second home. It could be a good investment strategy. But, there will be property taxes, insurance, HOA dues, maintenance and in some cases a mortgage payment so owning a second home is not free.
One way to look at it is if the second home is appreciating at at amount equal to or greater than the carrying cost to own the second home, it could be like owning the home for free. And, it is also somewhat of a savings account. The day could come when the equity from the sale of a second home could be used to pay for home care or assisted living. However, owning a second home is one more thing to take care of in terms of maintenance. Be assured, if something can break it will break.
And, then there is the car situation. If you own a second home unless it is within reasonable driving distance, it means flying there whenever you choose to visit your second home. That could mean at least one car based at your second home, which is another expense. If your retirement income is significant, none of this may matters; but if owning a second home is preventing you from otherwise enjoying life, you should consider the cost. Decide where you really want to live and focus on it as your principal residence. And, don't worry about grandchildren. With Face Time you can see them everyday and or visit several times a year with you going to them, or them coming to you. Quality time together is all that matters wherever it occurs.