Another fellow NCarolinian here, with 4 kids, too! We purchased 150 BWV points in Dec.1999. At the time, our kids were young, and I *thought* 150 would be plenty of points(Boy, was I wrong on that!) Less than a year later I purchased 50 points at HH so I could spend a night or two every other year on my way to/from Disney World. We usually drive(it's about 9 hours one-way), and I thought a night or two on the beach would be a nice way to break up the drive. Needless to say, I ended up adding another 50 HH points later for the 11-month advantage in the summer. You seem to have a good idea of how you would use your points(something I did not even think about when purchasing), so the purchase itself should be easy. Resale is definitely the way to go for HH right now. I would suggest purchasing a minimum of 75 points there, to bank/borrow for a trip every other year. The Saturday night stays are a killer there, so you probably won't be spending a lot of Saturday nights there with 150 points! For purchases of less than 150 points, you'll have to go resale, so you may not be able to choose your use-year. Just look for a contract with the right amount of points first. After closing on your HH contract, you can purchase your on-property points from Disney(keeping your same use-year if you purchase less than 150 points),or go the resale route again, but maybe ending up with a different use-year. I have to admit that having the same use-year for my multiple contracts is nice...it makes tracking my points usage easier. An ideal use-year for Spring/Summer stays would probably be Oct./ Nov./Dec./Feb. Any month would be fine, but you will have more flexibility with points that will not expire near the times you wish to use them. I have a Dec. use-year, and that works great for us because my kids are all teens now(18,16,14,13), and we have to vacation during school/college breaks, which means summer and Christmas/New Years. If I had to do all over again, I would have purchased a small contract through resale, then added on through Disney as I needed to, paying cash each time. It is getting increasingly harder to book BCV/BWV/WLV stays during popular times without the 11-month advantage. If you can be flexible with your summer dates and resort choices, where you purchase your points won't be a problem. But if you only want to stay at one of those three resorts, you should purchase points at one of them. We spend a lot of time at OKW, even though we do not own there, because my husband loves the bigger rooms and the general "feel" of the resort. My kids love the location of the BWV(not neccessarily the resort itself), so having points there is nice for Christmas/New Year stays when the 11-month booking window is needed. Good luck with whatever you decide to do!
I just wanted to add that the drive from Greensboro to Disney is not bad at all! We live just 35 minutes south of you, and we have made the drive in as little as 8 hours(DH, the professional driver, drove all the way, from midnight to 8 AM, and we stopped only once)to 10 hours(our last trip, the day after Christmas). Traffic is generally not bad, except during bike week/race week near Daytona, and holidays. If you plan on driving to HH, you are halfway to WDW from there! You will find it easier to maximize your points if you drive...you are not at the mercy of the airline schedule when booking your arrival/departure days(it will be easier to stay Sun.-Thur.nights).
