Wanted to post an update since everyone here gave me some good advice overall - I appreciate everyone's comments. Were looking at ~11 days - October 22 - November 2.
Below is a breakdown of my flight booking:
1) Matched my Delta Platinum status to Alaska Air. Received MVP Gold 75k which includes free upgrades
2) Signed up for the Alaska Air credit card from BOA - immediately spent the required $1000+ on an insurance renewal
3) Waited a month for the bonus to post with statement close - which gave me my companion ticket
4) Booked a flight using MVP Gold 75k upgrade and the companion pass - immediately got upgraded to first for the flight there with the wife. Yay! On the waitlist to get upgraded on the flight home. In the meantime though since I'm 75k I have platinum economy upgraded seats atleast.
5) So I still have the miles to use and the guest upgrades that I can use on a future flight. Very nice overall.
For hotels, I'm planning to stay 4 nights in the Ritz Carlton - followed by using a 7-day Marriott voucher on Wailea Beach Resort. I figured mixing it up with hotels on different sides of the island could be a good way to mix it up, no?
Now with that said, I have a couple new questions
1) What are my chances of getting upgraded for the flight home? Currently I see 4 available first class seats (that can be purchased outright for ~$1.5k) for OGG -> SEA, and plenty (6+ first class seats) for SEA -> IAH.
2) Should we rent a car? It would be convenient with having our kid with us where we can strap in and leave the car seat... HOWEVER, it looks REALLY expensive IMO. I'm looking at $500-650 for just the rental - add on top of that $30 PER NIGHT for a parking fee at each hotel. Overall I estimate $1000. Should we just use taxi's / ubers? Would appreciate any input from others that have traveled to Hawaii.