Well, if you move to the Big Island the real estate prices are actually really reasonable. You've probably picked up that I'm in IT too. Tons of jobs in the hospitality market, but it seems to be kind of shitty employers. I'm a higher ed guy, so unless something opens up at UH there, it probably isn't going to work out for me.
All this being said, if you're wanting a beach and Hawaii isn't a must-do, we went here in September:
Excellence Riviera Cancun. Was easily my favorite vacation of all time. Our goal was to stay at the resort and do absolutely nothing. Mission accomplished. There's tons of stuff to do if you insist on leaving, but our goal was to drink and eat our faces off.
They have a full open bar in your room restocked daily. 7 (?) sit-down gourmet restaurants with no reservations required. Sometimes we ate two dinners a night. This was $2600 for two people direct out of Richmond. You're mentioning family, so this might not be an option since it's adults-only.
If you knew me personally, you'd know I hate going to the same place twice, and I would go to Excellence every year if I could. It was that good.