My son loves his Ironman with the velcro band. Make sure it is a band and watch that gets wet. The Candidates may not have a watch during Indoc, but after then can.
As for luggage, you may want to go and buy a nice rolling duffel bag. This can double as report luggage and also sea year luggage. My son got a $30 rolling duffel from Walmart which has held up quite well through first sea year lugging books and the like. A sea bag is also good, but they will be issued one of them during indoc.