Am I Doing This Right?
 

If you'd be so kind I would appreciate some feedback. I'm relatively new to this credit card thing. So I want to make sure I'm doing it right to meet my goals.

Goals: free flights to Hawaii, Orlando, and possibly other destinations about once a year for a family of 4 (two adults, two children). We would fly out of Las Vegas or Los Angeles. We do not have any airline preference.

Credit cards we have currently:
Citibank Dividend
Capital One Venture One
Amex Blue Cash Preferred
Marriott Rewards Credit card
Chase Freedom
Disney Rewards credit card

So far, we're getting cashback rewards from the Freedom categories, the Blue Cash and the Citibank and then using the Venture One for everything else.
Is that what we should be doing or should we do something else? Credit is good so we can probably get any credit card.

It looks like all your cards are of the cashback type. The quickest, most efficient path to free flights is large credit card sign-up bonuses. Think airline cards and cards where you can transfer points to airlines (Chase Ultimate Rewards cards and Amex Membership Rewards cards.) From Las Vegas, maybe consider getting two Southwest 50K Cards and obtain Companion Pass for 2016 and 2017. Do some research on that to ensure your points all post in the right year.

Your biggest issue is not what you are doing right or wrong, but your goal is too big to achieve.

You have 4 people but only 2 people can earn. Given that the non-earning are children, it means that your travel will have to be done during holiday travel season. With that in mind, even you have all the points, you may still be able to have difficulties scoring 4 award seats.

Your best solution is to churn both WN card and CSP. With both cards, you should be able to boost 95K RR points at first. However, both cards have a 24-month rotation. It means you can only earn 95K bonus per person for each 24-month.

Then you will need to catch WGA fares as low as possible to reduce your RR points usage. The advantage of RR is it does not have an award "inventory", so virtually all seats are open to grab. The bad thing is during holiday season, WGA fares will be high. It means you will need to spend more RR to get an award.

Since you are not a frequent traveler, other programs in fact work against you (as your focus is redeeming peak season tickets). So there is no point earning something that you have difficulty to redeem.

In your case, since your only hope is on the bonus, you feel free to keep using your existing cards. However, I will suggest to consolidate the Disney card and Marriott after opening the WN and CSP cards.

What about the Venture One? Isn't that a card for flights?
We have the sign-up bonus for that one and we haven't used it yet.

Initially, since we are not frequent flyers I thought that cashback was the best way to work this because it offered the most flexibility. If we earn $1000 cashback, for example, then that's effectively $1000 towards any flight.
I think that logic still works but to actually get free flights we need to do something different/something more. Thanks for the tip :)

Thanks, I'll look into that.

Right now Southwest is not flying to Hawaii but I guess maybe they will start next year? Is that why you're suggesting Southwest? I hadn't considered them in the past because they don't fly to Hawaii.

Oh, I should clarify. We're not completely tied to a traditional school schedule.

That makes a lot of sense. So spouse and I will each get cards with big bonuses and churn those cards to get one free flight for the family each year.

Thanks so much for your help!
:)

This logic still works. However, the traditional wisdom is not to apply for a cashback card unless either the card has an opening bonus, or if not, the issuer allows conversion.

WN's HI service will begin eventually. Based on WN's current business model, there is no need to order B737 ETOPS. So WN's order means WN will extend to destinations which the flight path will be over water.

WN RR program may not be the best FFP, but it is definitely the friendliest among causal travelers. In fact, if you take some time understanding RR, you will know that the current RR 2.0 works as a rebate system, rather than a FFP.

Your chance may get improved. However, scoring 4 award seats altogether to popular destinations can be PITA.

The issue is there is a rotation and some other programs may not work for you.