I can sympathize. I used to agonize over our vacation budget, and spent oodles of time scouring the internet trying to "maximize" everything. Even after securing a hotel reservation, I would still look, and occasionally rebook to save $15 on the rate, or this one included airport shuttle, or this one had free breakfast, etc. etc. Re-price and rebook rental cars over and over to save $20.
At some point in time, I realized I would much rather spend my own time doing something else. It wasn't worth the hours and hours I was pouring into this to save $200 by the end of it. I do know some people find joy in doing that, and I did at one point in time. But things change, circumstances change, etc. I now just find a price we are comfortable with, and book the things we want. I have peace with the fixed price and don't "waste my time" re-shopping it.
That is why we made a full-price offer and were done with it. We could make the math work. And on a small contract, the $1,000 or whatever (most likely less...), we could've saved just wasn't worth the headache over the life of the contract. We wanted that price point at that resort, and didn't mind the use year. We just wanted the contract, and wanted to start planning our next trip with our family. One of the best things for our family is having that trip on the calendar to look forward to, and having control of the reservation (why renting wasn't going to keep working for us).
The difference of $5 per point, on a 75 point contract is $375. Is it worth saving that? Or would you rather just have the contract? Over 16 years, it is $23.44 per year. (Assuming you are not financing) Everyone has their own thresholds for things, circumstances, etc. and those are questions we must answer for ourselves. Personally, I just gave up on trying to make sure I got the "best deal" all the time.