You should be able to access the point charts for each resort on the
Worldmark Resort Gallery. Focus your study on the Red-dots for locations native to the WM system. (That is, ignore the other colored location dots ... most or all of these are not offered to resale owners.)
For legacy properties, and a handy rule of thumb, 10k is 2BR week in high season, standard unit. So, 40k is a really large account unless you plan to frequently book Penthouse, Presidential or other specialty unit types/locations.
Theoretically, the dues are paid after one gets their points but this picture gets muddied as the years roll by. To work the example you go back to the original developer sales. The membership came fully loaded with points and dues were paid later. I suspect the pre-pay of 2019 dues is likely to expedite closing (it may now be a transfer requirement??) Might be worth asking the broker/seller to clarify what was intended by pre-paying the 2019 dues (calendar year vs WM anniversary year)? and when will the buyer's first dues obligation begin?
Dues can be paid in quarterly chunks using WM's autopay system.