My husband and I are in our mid-50s and planning to retire in about 10 years. We've lived in Chicago for the past 30 years, but both of our children now live in Manhattan.

Recently, I've been considering buying a one-bedroom co-op in Manhattan (under $500,000) as a second home. Ideally, it would be a co-op that allows subletting, so we would have some flexibility if we weren't using it. We would keep our primary home in Chicago.

We've never owned a second home or vacation home before, so this is all new to us. I'm especially interested in hearing from people who have purchased a Manhattan co-op with sublet privileges. What has your experience been like? Were there any surprises or challenges?

At one point, we considered moving to New Jersey to be closer to our kids, but home prices there are much higher than we expected. We also realized that leaving the city we've called home for 30 years wouldn't be as easy as we had imagined.

For those who own a second home in Manhattan, is there anything we should be aware of before buying? Are there hidden costs, co-op board issues, financing challenges, or other factors that first-time second-home buyers often overlook? We'd appreciate any advice or lessons learned.