Alright I'm a great advice giver when looking at other peoples issues BUT a horrible decision maker and procrastinator when dealing with my own so I figured I'd ask. I will be coming into a chunk of money in the near future, nothing that would set me sailing off into the sunset but a decent chunk none the less. Here's where I struggle. I have personal rental properties that are about 50/50 mortgage to current value with about 10 years left on them and they are at 3.75% on 15 year terms. The sum of money would pay almost half of that debt down leaving about 5 years left to free and clear. The problem is that I am a really late bloomer when it comes to traditional retirement savings. Until several years ago I really had nothing but a savings and checking account besides rental property. I now have a PSP from work that is pretty close to a max 401K annually, a Traditional IRA, and a few retirement CD's, that's it. I've come into similar amounts of money twice before and other than putting down payments on houses I mostly pissed it away. I have no debt and no expenses, company pays for my health and auto insurance, gas, maintenance and such and the Wife, who is one helluva lot smarter than me and saved a sh!t ton over the years, pays for everything at home. Would you pay down the mortgages or perhaps invest it another way? And no the new Corvette is not an option this time.