Welcome to boating, just dive in and start learning. I would caution you that a 30' sailboat won't have much room, sort of like a four person tent. While one can live is that small a space, be sure that you want to...
Regardless of how small a space you can accept, we are all accustomed to certain creature comforts nowadays, such as running water, hot water, gas stoves, refrigeration and devices running off AC power. Now you can enjoy these comforts on a boat too, provided the boat has the necessary systems and you can connect to external power and water. Most of those necessary systems aren't common in 30' boats, you may need to go to a larger boat or look around a lot. You want: AC shore power, inverter/charger, cold plate/refrigeration, water heater, pressure water. And then there is the question of heat...I would suspect even in VA you will need heat in the winter, and you need a better solution than a space heater...maybe diesel or propane.
If you do, you will want to live in a slip, not on a mooring. you might check locally to see who permits liveaboards, and what they charge so you have a better understanding of how cheap or not living on a boat maybe.
Certified...in several regards...