bruwery
TUG Member
We're ok with booking far in advance (I'm already pretty worried about 2010, since we won't probably buy anything until fall and we're going to Orlando in Feb.)
If you're not buying until fall, it could be quite difficult to obtain a Feb 2010 reservation. You might consider looking at a rental so you can establish a comfort level with the place before committing to a maintenance fee.
And I'm still not sure we can make the check in day work for us -- which is why DVC (although very expensive) works great for us -- we usually travel on Tuesdays, or at least mid week (it can save us over $1000 in airfare for the 3 of us, and give us a direct flight instead of a total of 9 1/2 hours each way connecting in Toronto)
That's going to be a problem with any weeks based resort. As much as I enjoy my Cypress Pointe timeshare, you might be wise to consider Wynhdam points. They can be obtained on the cheap - and since Wyndham points transfer on resale, you wouldn't have to deal with paying a $2,995 fee to Diamond Resorts to convert to points.
Disclaimer: I don't own Wyndham points, so I can't claim to be the leading authority. Take my advice for what it's worth...
I've seen you posting on the HGVC forum, too, so I know you've considered that as well.
Whatever you ultimately decide, it's good to see someone being patient and doing serious homework.