1. How hard is surfing?
It's pretty easy, but like many new things, you just have to trust yourself and be ready to get back on board after a fall. Most rides even for professionals end in a fall, they just add a lot of style. The goal is to be grateful for the warm, clean, clear water and the awesome ride.
2. What should I wear?
A tight, long-sleeve rash guard and good fitting board shorts, plus lots of non-reef scarring (free of oxybenzone/octinoxate) sunscreen lotion is recommended.
3. Where is a good place to surf?
Generally, at first you are looking for a sandy bottom and knee high waves. Hanalei and Anahola are two of the best places on Kauai for that, but mostly just during the summer as winter waves are for the experts only. Poipu has good waves year round with some bigger swells in the summer, but you have to be careful of the sharp rocks in some places. Also important is to wait a few days after heavy rain before entering the water. Brown water is not good water. Kiahuna has a great beginner break as well, but can get crowded.
4. What is a good board to learn on?
Width is your friend. You also want to make sure the volume of the board supports your weight so that paddling is easier and the board glides ahead of the wave while you are standing. So choose a wide board a foot or two over your height. Too big of a board is hard to paddle and turn, too small of a board is hard to catch and stay on a wave.