After several weeks of reading/learning/researching on this board and several blogs, I am ready to building points for future trips. But I'm still too wary to make the leap without some feedback first! Here's my info:

Family of 4, just north of Baltimore. Frequently use BWI but can also use PHL or Newark. Try to avoid the DC area airports, but they are possible as well.

We've almost always just taken short haul flights on SWA from BWI. Usually to Orlando and other east coast destinations. Have a trip for 4 to Orlando planned for Summer 2013. Want to go to Hawaii in Summer of 2014. Also would like to start seeing some of the west coast.

My wife teaches so right now we are primarily limited to Summer travel for anything more than a long weekend. We would like to start taking trips to Europe in the Summer and when she retires in 5 years add in trips to Asia. For the long haul flights we would prefer to fly Business or First Class (who wouldn’t!). We will also need to build up hotel points.

Our credit scores are both in the 780+ range. Current cards in use are Discover, AMEX Blue, Chase Freedom and BOA (rarely used). Currently have 40k in UR points.

My plan
1) I will apply for both Personal and Business SWA cards. Hit the spend on both in January to get the Companion Ticket a few months later.
2) Both of us apply for the BOA and BOH Hawaiian Airlines cards. Use the points for Hawaii or transfer to Hilton points.
3) Both of us apply for the AMEX Starwood Preferred Guest card.
4) One of the many Chase cards. Open to suggestions!

Then next month I’ll cycle in Citi AAdvantage cards.

Does this seem like a good start? Thanks!

Tony