Scaredy, i lived in the Discovery Cortez Hill building and loved it.
Some positive points: easy access to the 163, quiet area with minimal vagrants, large rooftop pool (for a condo tower), traditional doorman, hill location means good views on the lower floors.
Main downside is that Cortez Hill is almost all residential and walking to downtown itself is a non-flat mile long walk.
My patio was about 20×30 feet!
No reason you have to buy now. Get a 2-3 month airbnb here in ocean beach and see if you like it better. In many ways we are more walkable: short blocks, slow moving traffic, businesses spread out more. Hillcrest and PB are similar. As I recall, Hillcrest is the most dem neighborhood in San Diego, about 92-8 Hillary over Trump.