My tidbits...

Get a good man bag. You will be carrying more stuff. Most important, you should be walking around with your passport. Personally, having important stuff spread around multiple pockets is a creative way for me to lose something. I use the Maxpedition Remora.

For short trips of 2 weeks or less, I use Verizon's new "Travel Pass" feature. It is a good option if you just want to get there and spend a week looking for a better long term option.

Upon arrival wherever I go, I try to go grocery shopping and stock up on water. I just went to St. Maarten (Dutch). One day, the city cut off the water for half a day for maintenance, no warning, and locals were acting like it was not a big deal. So, I don't assume the mindsets are going to be the same. People may fundamentally think differently.

Have fun. Don't over prep to the point you can't have a good time. Your knowledge and know-how is your best prep. Many times, working through issues leads to the best stories and ends up being the most endearing part of the trip. Also, learning how to do more with less is a valuable survival skill.