@Kelen Weathers I can see the struggle here!! This resonates with me because I’ll be in a similar situation soon. I tend to be a more risk averse, because I feel that allows me more options if the economy shifts. You are already an investor and landlord so the initial learning curve is not a consideration. Likely will be much easier to buy this one and rent it than the first. If I were going to buy another property before paying off the student debt, I’d want to be triple sure that the numbers were still healthy in the existing property after the cash-out refi , and make sure my cushion for vacancy is reasonable. Then buy a reliable, cash-flowing property that will not require a bunch of time & money to rent and stabilize (probably not going for a home run). But after that I’d get very serious about getting those student loans out of my life before buying again. Of course we don’t know all your numbers, Just be sure you’re not exposing yourself to too much risk here. Best!