I agree with the last paragraph.It's a bit muddied because of the upcoming trips for sure.
So if I'm understanding correctly the only trip the direct point purchase covers is the $4300 for the June stay that would now be 302 points. You will still have to try and rebook the July trip which will be more points and more MF's. If so and you consider the MF's on the 100 2109 points (plus the 200 2018 points) for the June trip it's more like a $3,500. So closer to paying a $2900 premium to buy direct which if you can use the benefits to consistently purchase Gold AP's isn't terrible. The bigger comparison is if you purchased all 200 resale and took the approx $11,000 difference to use towards the future AP purchases.
Or you could consider a smaller 100-105 point direct purchase and use banked 2018, current 2019 and borrow the 2020 points for the June trip and then continue to look for a 100 point resale contract. Maybe even a different resort to give you 2 different home resorts that you'd rotate staying at with banking or borrowing.
Rescind and change to a 125 point contract for AKV that allows you to bank and borrow to still keep the June trip.
The remaining “75” points you were going to buy direct for $171 = $12,825 which will get you a 100 point BWV for the same price.
Even if you still have to pay cash for the Sept trip, for about the same price as you’re spending now for 200 AKV direct, you’ll have 125 AKV direct, and 100 BWV resale.
That gives you lots more options over your contracts. And the 125 is plenty for perks and banking and borrowing later to stay in one of the newer resorts.
Just tell the guide you decided you want everything (the preplanned trip) except you’d much rather only buy 125 points. You don’t have to tell him about the resale component of your decision.