Here are my specifics, you may be able to save time and money...
Signed up for two southwest CC (1 personal, 1 business) and do the minimium spend (just normal purchases) and obtain 104000 points.
Do trick to get to 110000 points and get free companion pass (worst case, buy 20000 hotel points and convert). $190
110000 - 30240 points, (3 tickets detroit to orlando + free companion pass, $5 per leg) + $40 to use reward points
79769 points remaining
Rental car through
alamo rented through southwest rewards portal, $169 bonus 2400 points
82160 points remaining, total spent $378.
Detroit to Nashville for 2 people (1 through points and free companion) 10080 + $20 and 72080 points remaining
Detroit to San Juan for 2 people (1 through points and free companion) 24744 points + $20 and 47336 remaining
Detroit to New Orleans for 2 people (1 through points and free companion) 12000 points + $20 and 35336 remaining.
35336 points is enough for a SECOND trip to disney for the family.
Next year wash rinse repeat with my wife getting new cards, we've done this twice now.
Kids get Disney vacation and the wife and I get 2 additional vacations. Don't discount the cost of wear and tear as well as gas.