Hard time deciding when to purchase

Since dues are assessed and paid on an annual basis, you pay prorated dues from actual date of signing the contract, no matter what your UY is. So the later in the calendar year you sign, the less you pay for dues.
Yes, I understand that.

I’m unsure if signing on May 1 vs May 30th makes a difference. Is it prorated on a monthly or daily basis?
It's daily - they will list the number of days for which you were responsible for your dues not the statement you get after you close. And, just a small quibble, they will actually prorate from the day you tell your guide "yes, I want X." If you wait a few days to sign, you won't save any dues for those days between in between saying yes and signing.
 
It's daily - they will list the number of days for which you were responsible for your dues not the statement you get after you close. And, just a small quibble, they will actually prorate from the day you tell your guide "yes, I want X." If you wait a few days to sign, you won't save any dues for those days between in between saying yes and signing.

To expand, it’s the day the contract gets drawn up…which is typically the day you say “yes”!
 











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