I have been to Hawaii 4 times, all islands but Molokai (tho we landed there on one island hop but didn't de-plane) I've been to Oahu once and to Maui 4 times. Maui in my opinion is NOT what it used to be, it's expensive and highly over-rated. It is also VERY crowded. I remember when there was only ONE stoplight on the entire island and you could actually make the drive fromKaanapali to Hana via the Hana highway in one day's RT. The nightlife is excellent in Maui for couples, but I think it really is more of a "resort" island, where Oahu is more multi-cultural and lifelike....sure it is crowded and has it's pros and cons, but as reading what was said above, your rent and cost of living would be better on the main island not to mention cheaper and easier to get flights on and off, and island transportation is much better and more readily available. I would think job market would have more to offer in Honolulu than on Maui. LOTS of tourists swarm the Waikiki area, but Oahu is a bustling island with its military, seaport, air traffic, research and industry. I would recommend Oahu especially to young folk such as yourself. You could take a ferry or fly to any of the other islands to visit and check it out. Good luck!