When I’m on a hill and starting from a full stop, when I take my foot off the brake, the car will start to roll backwards (even though I’m in Drive) until I push the accelarator pretty aggressively. I thought automatic transmissions are supposed to “hold their place” on a hill. Is this normal or an indicator of coming transmission problems?

Every car with an automatic that I’ve owned since the 60’s will roll back until I press the gas.

Automatic transmissions are not designed to “hold” you on a hill. That’s what brakes are for! Having said that, you should not need to push the gas “aggressively” to take off after releasing the brake, unles you are heading uphill on Lombard Street in San Francisco.

Check your fluid, and also have a good independent transmission shop check the adjustments.