Hi, Stacie!
You raise some great questions regarding DVC resale properties. I suggest that you check out
Disney Vacation Club's website or call a Cast Member at (800) 500-3990 to ask about resale properties as well as the specifics of Member Benefits. These things change from time to time, so you'll have the most accurate and up-to-date information if you speak with a Cast Member directly. It's a big decision, so you need to know that you have all of the facts straight.
That being said, as long as you plan ahead, you really shouldn't have many problems getting your choice reservation. The biggest tip for getting your first choice is to book your vacation as early as possible. If you can book your vacation at your home resort up to 11 months in advance, then you should carefully consider which resort you'd like to call home, and be sure to reserve your villa when the 11 month window opens. That benefit really helps you get a special reservation such as Thanksgiving Week, Christmas week or, in our case, a Theme Park View 2 bedroom villa at Bay Lake Tower over the Fourth of July holiday. (Wishes Nighttime Spectacular was in our very own backyard!) If you can't plan that far in advance, but can be a little flexible with regard to moving your trip by a day or two, or considering an equivalent villa at another property, you won't be disappointed. Every DVC resort has a special flair and unique personality which make its Home Resort Owners proud!
You can also be asked to put on a "Wait List" for a property which isn't currently available, but may become so in the future. This way, you'll have a villa to call home, and your reservation can be moved over to your first choice location, should it become available.
Please send me any additional questions you may have regarding your trips to WDW or Disney Vacation Club Membership! I love to help!