Hi All.

I've been absorbing a lot of information over the last few weeks and have learned a huge amount - almost too much to the point it's becoming a little overwhelming.

I'll try and describe my situation and goals and then ask a few questions to see if you guys can help me with some clarity.

Family: 2 Adults, 1 child (3) and one infant (6 months)
Home Airport: San Diego, CA
Target destinations in next 18 months: Mexico, Hawaii, Costa Rica, Bahamas, San Fransisco, Denver, Tokyo (Family), Sydney, UK (Family)
Reasons for trips: Family vacations of 5+ days leisure only

Current cards: US Airways Barclaycard - 55,000 miles + $99 companion passes
Future Airline cards: SW Personal & Business (targeting the companion pass in Jan 2016 for 3yr old) Citi AAdvantage, Chase Sapphire+Freedom, Amex Premier Rewards maybe Avois??
Future Hotel Cards: Hyatt, Marriott, IHG, Club Carlson

Based on our location and most of our proposed target destinations it seems that SW Airlines would be our best focus for travel which is why we want to try for a companion pass for our eldest child (infant will be good for another 18 months in lap). Is this a wise decision?

I hear a lot of talk about utilizing Avios for short haul flights on BA. Is this only a good deal when spending AVIOS on BA or does the case still hold up when using AA points to book BA short haul flights? Can I pay for BA with AA or AA with Avios??

For our Tokyo goal I'm looking at AA off season flights, but I'd like to spend some time in Hawaii on the outbound leg and Sydney on the return leg from Tokyo. As AA have killed the stopover, am I better going for another Group/Airline/Points to create this route?

Thanks for any help with these basic first quesions.