Google Maps is great, especially if you do most of your planning on a computer. You can create maps with your own landmarks, indicators, and share it with people. It was really nice to be able to whip the phone out and see what was nearby without having to look at a list first. The map was the list. Google Maps and Google Trips don't speak very well to each other, and it's a little clunky when it comes to sharing it. We relied heavily on this while planning what we wanted to do, and used it while we were trying to find something new to do in NYC.
I love Hawaiian Airlines. I like the service and I'm generally willing to pay the premium on their tickets because of it. Since I like flying them so much, and because they do a lot of direct flights from major cities, I signed up for their promotional emails. I also encourage people who want to fly with them or are looking for good sales to sign up for it.
Hopper is an app that monitors flight fares across all airlines. Promotional emails are good, but something monitoring them for you is better. You can set dates in the app, and scroll through different months to be able to see the trends throughout the year. This is a little bit more convenient because you'll get notifications instead of checking your spam folder. This was how we knew when to score our $800 tickets, round-trip, direct flights to NYC... on Hawaiian.
Neither of us have been somewhere cold. Ever. We used OneNote to keep track of our flight itineraries, Known Traveler Numbers, budgets, research on cold weather, checklists, you name it. It's easy to share, and available on literally any platform.
$80 for 5 years? Why not? It's useful if you're flying domestically. You could also do Global Traveler, which I hear is a little bit more stringent and costs more. Either way, it becomes easier to travel through TSA without all the nonsense about liquids and shoes and computers. I'd give yourself at least 3 months before your intended travel dates, just in case it takes a while. I think it only takes about 6 weeks but better safe than sorry.
Youtube makes it to the list because it helped me stay excited for the trip. 9 months is a long time to be planning something, and the time equivalent to having a baby. Youtubing things people like to do, see, eat... Or maybe things you want to do, see, and eat will help you get an idea of whether or not the experience is one you want.
Tam used a referral with Lyft to get $5 off our first 10 rides. Definitely a good deal around the city, especially since we used it less than that! Sign up before or after your flight to maximize the time limit they have on you redeeming your referral promotion.
Ask all the questions!
I think something that helped our vacation was my willingness to ask my former coworker what he did. People are generally willing to answer questions. The most anyone will ever say to you is no (or some equivalent to it), so ask away!
I think that's about it for our preparation. Other apps came up, but I'll get to that since it's a large part of our storytelling. It might be boring, but is totally necessary to having tons of fun!