Thanks! I've been consuming content for a while now from here and all of those sources you mentioned, and over the past couple of years have tried a couple of times to get up to speed. I've definitely been learning a ton but still feel a bit rudderless. I do have a concrete goal for travel next year, but only a hazy idea how to reach those goals.
Ask away here! I think you said you're planning on Aulani next year with your mom for milestone birthdays? Would you both be traveling from the same airport? If so, I suggest considering a SW CP to be on your list of goals for the airfare part. Depending on if that trip is in the first half or the second half of 2022, would determine your timing of applications for SW cards for that, and you'd likely have to do a MDD. SFF has covered SW CP extensively on this thread (just use the search for "CP" in this thread with
@SouthFayetteFan). You have the $200 airline credit on the Amex Plat that you could squirrel away SW travel funds (in <$100 increments, ask if you need clarification)...but they need to be used for travel within 12 months of original booking so keep that in mind and know they can only be used for flights (not early bird check in, etc).
Did you say you have AA miles? You could use those to go LAX-HNL and they're currently showing 20K one way per person. Sometimes the AAdvantage shopping portal is a good way to earn more miles, as well as the AAdvantage Dining program, and SimplyMiles to earn some AA miles too. The nice thing with points is that you can book one ways on points with two different programs if you don't have enough in just one program to cover all of it. For example you could go one way on SW points and go the opposite direction on AA miles (or UA miles, or whatever "costs" the least). I'd only do that if I could cover both ways with points or miles, because I've found that cash one way tickets are exorbitantly expensive.
Aulani is out of my wheelhouse, but surely there are folks here who can cover that part of it. The Amex travel portal can get you a 1 cpp redemption for your MRs and if you book some of the nice hotels on there some of them come with free breakfast for two, and often a property credit. Aulani isn't on there though on random dates I checked.
I've heard MS is dead in your general geographical region, but if I were you I'd pick up the prepaid $500 gift cards (VI or MC) at the grocery store with your Plat and try to pay as many of your expenses with those to rack up your MRs.
Ask as many questions as you want! We're a very friendly group.
P.S. Would your mom consider being your P2?
ETA: The fastest way to pick up AAmiles is, of course, through a SUB lol. I did find Aulani available as part of AAdvantage Vacation Packages FWIW.