My tenant skipped out on his 2-year lease. I want to take him to small claims court to recoup 2 months rent. If I can’t rent the place beyond the two months, can I return to court to recover another month’s rent from the ex-tenant?

It depends on your state’s rules. Generally, a party must bring all claims arising out of a particular breach at the same time. This is because courts don't have the time to hear the same case 7 times. Here the breach is skipping out. You'll only get one suit. You have 2 options: 1) voluntarily dismiss the current suit and re-file when you've rented the place and know exactly what your damages are, or 2) amend your complaint to request rent/late fees/costs through July "or damages as proved in court." With number 2, you don't get rent past July, whether you have a new tenant or not.