I gotta say something...im confused. You mentioned going to Sandals for the anniversary instead? What's that about?? If you cant afford DL, how can you afford Sandals?? Seriously I think you need to take another step back. If your MIL cant maintain the taxes on a rental property and the home she lives in, you should be taking over her properties for her and managing her money. It sounds like she sucks at it and you're lefting holding the bag because your DH doesnt have the backbone to stand up to her. She can stay in her house, but you guys need to take charge of her finances so you can make sure the taxes are paid and there's money in the bank for her needs in the future (like a new motor.) Also - sounds like you had some awesome vacations and that is cool, but seriously you guys need to put more money in the bank. Even with everything you said, it sounds like you didnt have enough money in the bank to start with. You're seriously 9000 in cc debt?? He was driving a 99 jetta?? You can make the choice to keep blowing your money on vacations and being irresponsible and worrying about what the future holds (great youre working on retirement, but you have a serious cash flow situation IMO cause all the money is locked away...) or quit taking the vacations for 1 year, stay at home and then the money goes into a slush fund for vacations which gets replenished or paying the senile MIL taxes...