I bought a pair of Ronstan boots (RFCL62 at APS). I've worn them a couple times so far. I thought they would have better arch support because they look like they have the sole of a cross training shoe. Turns out they don't have very good support. But they do have plenty of room to add athletic shoe insoles, which I did, and now they work great. The boots were welcome last Sunday when we sailed in 40 degree weather. I even had to add a pair of poly socks it was so cold.
I have worn both Douglas Gill and West Marine hiking boots. Both seem to do pretty well and last for a few years.
When the water gets warm, I sail with canvas Converse All Stars. They seem to last a long time and are comfortable. They offer some ankle support and will dry out quickly. You can even get colors to match your boat!
Good for you to race in your first regatta! Fun, isn't it? And good for you for hiking enough to rub your ankles raw! I wear Magic Marine zip up booties. Not enough arch support to walk around on the ground much but I put them on before I go on the water.