Can We Afford a Vacation Home?

I received an unexpected payment of $500k from a former employer and I’m desperate to figure out what to do with it and how to plan for the taxes.Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoneySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

With a lot of kids and a lot of rental properties, we're wondering if we're on track to retire in about 16 years?Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoneySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I am 50 and have a plan to quit my job in about five years and move internationally where the cost of living is lower. Can I do it? Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoneySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

With a baby on the way in a couple months, I’d like to do a check-in to make sure we’re on the right financial track.Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoneySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Even though I'm quite sure we have enough saved, I'm struggling with what my next steps should be given my situation.Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoneySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Last Wednesday was May 29, which is also known as "529 Day," aimed at raising awareness about 529 college savings plans. I joined CBS Mornings to explain how you can take advantage of government programs for education.Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoneySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We are thinking about buying a second home but I am not sure we have enough money saved. Can we pull it off?Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoneySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

My wife (66) and I (68) are in our final two or so years of work and we're concerned that we'll be okay in retirement. What do you think?Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoneySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

My position was eliminated last year and I took a severance package in lieu of relocating and I need to adjust my retirement plans.Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoneySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What is the best way to financially help out the parents without hurting our financial future?Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoneySee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.