I feel I am ready for the adventure of points accumulation and successful free/cheap travel, but do not know where to start. Also I feel that our family is missing out on opportunities to double-triple dip in some situations, but I cannot figure out what to do. Any advice will be greatly appreciated.
Our situation:
Credit scores (both) - upper 700
CC: me – Costco Amex joined with hubby (opened 3-4 years ago)
Chase Freedom – joined with hubby (old card), as of now 2000UR
Chase Pref Sapphire - hubby (opened in Feb 2012), as of now 70,000UR
Amex Gold – closed 4 years ago
Spending: 3000 monthly (hubby) – job related expenses, 1000 monthly (50/50) – family expenses.
Club Carlson points: around 50K. Accumulated close to 200K last year (thanks to 2 big promos) and used them for 6 nights in Europe this summer. DH stays in hotels about 1-2 nights a month, not that much...
UA miles 16K (one account), US AIR – 12K (one account)

Due to the DH’s job we are able to use idine a lot. We have two idine accounts and we get around 500-600 dollars cash back every month. I was thinking about switching to miles instead of cash, but could not figure out if it makes sense. Now we are getting 15% cash back, airlines give you only 5 miles per dollar. 500 dollars a month or 15,000 miles a month, is it equal?
Our goal is accumulate as much as possible for travel to Europe, Asia, or within US for three of us. No dates or location are set, we also can travel only in peak seasons, since our daughter is in school. My DH hates to have a lot of cards in his wallet, but I think I will be able to keep everything under control and just give him one card in a time.
Where should we start?