Thanks for the additional information. It looks like the major US airlines fly from either GRR or ORD to OGG, so any should be able to service your Hawaiian needs. My suggestions would be as follows:

1. Get Sapphire Preferred and Ink Bold (both from Chase).
2. Get Starwood AmEx (American Express).
3. Get 2X AAdvantage Personal cards (Citi).

Put your spend on Sapphire / Ink Bold in categories in which you earn multiple points and put the remaining spend on Starwood. Spend enough to get the 50K bonuses on Citi.

Then, check back on MilesBuzz occasionally and a few times a year apply for cards with big signup bonuses, Hyatt, Marriott, United, etc. Churn AA Business cards every 6 months or so and Personal Cards about every two years. That should net you ~150K AA miles a year for little cost, enough to get two of you to/from Hawaii in Business class.

If they are 18, I would get your kids credit cards, preferably a no-fee card from AmEx (like the Hilton card). That will help them with establishing credit and all future AmEx cards will show the earliest membership date and help with average age of cards.

Do the above for as many of you as wish to. Not too complex but will earn you lots of miles and points, enough to enjoy some free vacations. If you want to get more complex, you can certainly get Chase Freedom, a Chase checking account, and churn 5-6 cards every 3 months. Up to you.