Took the Plunge....

pjgj13

And bought a platinum membership. Once I get my package in the mail, what should I send off first?

1. A 1969 proof set
2. A 1999 proof set (quarters)
3. A 1999 silver proof set

I know I have to use the 8 freebies at the same time. So what combo do you think I should send in first?

itsnotjustme

None of the above. Those can all go as moderns $14 and unless you get exceptional grades, are likely not worth the fees. The 8 freebies are good for regular service that normally costs $30 each.

Bochiman

Brian's right. Those are better off saved for something other than modern.
You have a year to use those freebies, right? So, go for some other coins....worst case scenario, your year is almost up and then you use it on your moderns.

(out of the 3 you listed, the 1969, unless DCAM or remarkably naturally toned, shouldn't even be considered, imho)