Thank you for sharing your problems.
1) I will usually perform a pap smear for patients around the menopause age, and if it is negative, I wouldn't do any further pap smears, unless there is bleeding or new symptoms.
2) This is a hard question to answer. The pain experienced could be attributed to various factors as follows:
a) The doctor/gynae/nurse performing the procedure
b) The size of the speculum (plastic device that's inserted)
c) Use of lubricants
d) Some clinics also use lignocaine (numbing) jelly before the procedure to numb the area
e) Consider treating the vagina with premarin cream if it is really dry and painful (need to see a doctor to get)
Take Care.