This is a tough one for me. You definitely have some spending habits that need to be fixed immediately. But with that salary and your expenses, it's hard to see why you are in so much debt. If it were me, I would focus hard on changing habits and paying off all debt and then consider an international move in a year or two. However, I love to travel and experience new things, and can see how this would be a huge motivator to get your life on track. If you follow that route, you have to sell both homes and get out of debt. Neither would make you money if they are rented. You would get a better return on investment by investing the equity, and a MUCH BETTER return on investment by using the equity to pay off debt.
Also, are you really certain about the cost of living in Europe? In my experience, everything is more expensive there (food, gas, rent, utilities, clothes, etc). Also consider what former player mentioned about your retirement. Could you move to Europe and still save for retirement?
It is difficult to know for sure whether you can afford this because you haven't listed all of your expenses (how much do you spend on food, clothes, gifts, donations, internet, haircuts, gym, etc)? Maybe if you use a case study format you could get more specific advice. A fruitful exercise might be to draw up your current expenses, being realistic about all your expenses, and a well-researched comparison budget for your life in Europe, assuming you sell everything and pay off all of your debt. In your European budget, be sure to include some money for entertainment/touristy stuff, make sure your other budget item items are realistic based on what you have been spending, and make sure there is enough left over to save for retirement. Can you make the numbers work?