Wow - what responses. I'm sure you're more confused than ever!
But so am I! I'm still not quite sure what your ultimate goals are. They could be:
1. Getting to 5* and converting all the timeshares to points
2. Using them all either at the resorts themselves or trading.
3. With lockouts, having between 4 and 8 weeks of vacation a year from timshares alone, in which case, you have to figure out just how much PFL is worth - just how many weeks can you take off?!
SDKath is the master of 5* but I repeat the advice I gave to you a week ago. You are, I think, putting the cart before the horse. You don't even own one yet but you're talking about owning four! As I said to you earlier, if you want Lagunamar in high season and you want to be in SVN, then buy there from the developer. But I would most certainly recommend that you purchase something like I just did - Mission Hills - first and requalify it. It will then get you 148,100 SO and 72,000 SP if desired.
If you were absolutely certain that you wanted 5*, then the best way is to buy TWO WMH or the like, purchase Lagunamar Gold to requal one and then upgrade your developer purchase to Platinum to requal the other. All that said, why not rent a place first and be certain you really like it. As you can see, selling what you own is not always easy and is almost always a pain in the neck.
In terms of points, this argument will go on forever. Yes, I would never have paid full price (or even half price) for Air France First Class, but I'm so glad we got to do it and we will never forget it. What's that worth??? If SP had not been so devalued these last two years, I'd be on the road to 5* myself. But look at all the airlines and you can see they have to make it harder and harder. They are all losing money and can't give seats away - and there are trillions of miles out there awaiting redemption. My plans for a Starwood Points IRA are gone! Earn em and Burn em!
In the end, you first must clarify exactly what you want to achieve. If you are even thinking about 5*, at some point you have to purchase from the developer. In that case, you should certainly buy a resale first so you can save a bundle.