You really should take a look at the Raddison Aruba. It would be your best bet points wise. You and your wife each get a CC card, and meet the min spend, i think its 2k, and you end up with 95k miles each. Then one of you just needs to put 1k more, to get to 100k miles, and you are set. The person with 100k miles books the first 2, and last 2 days, and the person with 95k miles books the middle 2 days.

So for a total of $150 bucks(First year annual fees), and 150k points, you can stay for 6 nights. Use your UR points to transfer to SW for the flights, and you are all set. If you friends dont mind playing the Credit card signup game, you can tell them to do the same thing. Makes for a very cheap vacation.

Also if you have a raddison near you, or somewhere you go often, the Club Carlson card gives you 38000 points every year with your 75 dollar renewal. This is enough points to stay in all but there two highest teirs, for 2 nights. Thats a pretty good value for the 75 dollars.