First of all, thanks so much to all of you for responding with your experiences. I feel prepared when making a call to retentions and am able to make a great choice due to that
Prestige, 1 year AF, spent ~10K the first year.
Offers:
$200 after spending $4k in 3 months (Rep may have misspoke - she started to re-read the promotion when I asked about the next option)
I specifically also asked for the bonus points on drugstores, and was offered (and accepted) a bonus 4x points on Gas/Grocery/Drugstores for the next 6 months, up to a maximum bonus of 50K points.
So... my plan is over the next 6 months I'll spend $12,500 at drugstores, pay ~$125 in fees, and earn ~62K TYP (which redeemed for AA flights is $1000). Totally worth the AF for that, plus the AA lounge access, $250 flight credit and fourth night free.