The best way to learn something is through experience. My commuting practices have also changed or evolved a lot in the 5+ years since I started. I started out commuting on an Italian racing bike because that's what I had available, replaced that with an English touring bike and finally settled on a sporting touring bike (several of them actually). I now have two sport touring bikes (Salsa Casseroll and Waterford RST-22) and just bought a third (Gunnar Sport). For my purposes, they are perfect for commuting yet versatile enough for recreational rides, trails and light touring.

Proper clothing is a trial-and-error process. Although cycling clothes are expensive, most are extremely well made and durable, so they last a long time.