Have fond memories of fifth avenue, downtown.
First, cook-your-own steak at the Gaslamp Strip Club restaurant (340 5th ave), then wander up to the Ghiradelli's chocolate ice cream shop, (643 5th ave), then a movie at the Regal cinema a couple blocks north of there.
Tons of things to spend money on in the Gaslamp. But, the Strip Club is a unique opportunity to get a steak dinner for less than $25 a head (I moved to Seattle a few years ago, I have no idea what it costs now or if they changed their operation.)
All I remember of Hillcrest is the time spent finding a parking space, Urban Moe's and Chocolat' across the street from there.