1 - I was thinking of buying resale at Vero Beach, I can get more points for less $ how difficult is it to book 7 months out at OKW? or any other resort?
I have booked at the 7 month window or less for almost all of my stays, and have gotten what I've wanted. I will say, we haven't been picky, and have tried almost all of the
DVC resorts.
We mostly travel in the summer and spring break. If you want to travel during peak times (Christmas, spring break, etc.), or stay in certain types of rooms (BW view, AKV concierge, OKW grand villa, etc.) it will be more difficult. Also, if you want to primarily stay at WDW, I would buy points at a WDW resort. As time goes by, who knows where Disney will build resorts, and how many of those resort owners will try to book at WDW. It may or may not become more difficult to book at Disney. Time will tell, though.
The best advice...buy where you want to stay.
2 - What are the financing options with resale/disney?
Disney offers financing, but I agree with a PP that if the interest is high. If you have good credit and can get a home equity loan, that's a much cheaper route. The longest term with Dis is 10 years (at least a couple of years ago), and they had a couple of other options (maybe a one and three year?).
3 - How quick can one close thru Disney? I know resale can take 2-3 months total.
When you purchase through Disney, closing really doesn't matter because you can make reservations right away. With a resale, closing ranges from 1 1/2 months on the low end and 3 months on the high end. We purchased 3 contracts through resale, and from offer to reservation was about 2 1/2 months.
4 - Why would you recommend going thru Disney and not do a resale??
Ease. I agree that the Disney transaction is easier, but the resale route wasn't painful, just longer. On my VB points, I saved $36 per point ($5,400). Because Dis was offering a heck of a deal during the 15th year DVC anniversay and Friends & Family promotion, I only saved about $1,200 on my SSR contracts. If I were buying the same number of SSR points today, resale would save me over $9,000 ($78 per point via resale vs. $101 per point via Dis).
One last thought. VB buy-in price is low, but maintenance fees are high. No fancy calculations, but I figured my break even point was somewhere between 10 - 12 years. After the 10 - 12 years, it would actually have been cheaper to buy points at SSR. We purchased VB points because we want to stay there at least every other year.
Good luck, and welcome to the Disboards!!!