Any update from OP?

Anonymous wrote:The thought of selling the investment property and having to pay capital gains on $300K makes me sick to my stomach for you. It’s better to keep it as a neutral investment. Are you seriously saying that you are a family of 4 with two sets of grands living with you!? If so grandparents should absolutely be helping with the mortgage. If they aren’t it’s time to have a discussion.

Why? That's the law. It's their fair share.

I would sell the fallback house and cut expenses where you can so you don't have to use much of the proceeds for everyday living expenses. If you pulled out $1,000/month, that $300k net could pay for 25 years of $1,000/month withdrawals. And you never know what might happen in the next 5-10 years that might make it unnecessary.

Are your parents able to help with the mortgage at all, or are they basically dependent on you?