We had same difficult question - because we waited too long (I'll explain momentarily), we decided to wait for Poly, but I'm having some regret.
So we just got back from a cruise (2 nights at WDW afterwards) this past weekend. We intended to see what deals were offered onboard, but we got busy the first day or two at sea, then had a couple ports. Then, unfortunately, my wife got sick, so I ended up not going and talking to the guide until the last full day on the ship. With my wife still not feeling well, we just weren't that enthusiastic in discussing it, and it was the last day. We could have done the paperwork at WDW after we got back over the weekend, but we just weren't into pulling the trigger yet. My wife couldn't get excited at that point for VGF either.
For us, we're looking at one more contract basically. We are currently at 318 points, all direct (118 at Copper Creek and 200 at Riviera). For the foreseeable future, I think 500 is about our limit when looking at the annual dues. $4,000 annually just on dues is already a bit to stomach, but at least it's in the range of what we'd pay for a week at a deluxe WDW hotel. Also, for background, we've financed our purchases through
DVC and would do so for this purchase (we have our reasons). Because we live in Delaware, we have to sign our contracts at WDW (or on a cruise). They can't send it to us to do in DE because DVC isn't registered to issue financing in DE.
So, because we waited until the last day and just couldn't fully evaluate how we felt adding on and felt too rushed at that point, we decided to wait. The deal was pretty good though, so I regret it a bit knowing it's unlikely we'll get anything like it again. The price for 150 points at VGF would have been $183/pt, before Magical Beginnings. If we took the $22/pt check, it would have effectively taken it down to $161/pt. At that price, we probably would have been in good shape to have sold our contracts in a couple years if we wanted Poly.
It's definitely a tough decision, and not knowing how much more expensive Poly will be with incentives (possibly $40-$50 more per point if there aren't good deals), not knowing which association it will be, or even what the rooms will be like, it's just really tough.
I doubt any of that is helpful - but just sharing.