There's no reason you can't contribute the max this year assuming you've made $5500 in W2 income. Same with the last year, you can always contribute up to your earned income. There's really only one year where you definitely can't contribute if you take all 3 years in a row. But I wonder if you can take it like a year on, 6 months off, a year on, 6 months off, a year on or something so you can always contribute.