1. Down for anything to eat/drink. I heard about piscos and terremotos
2. I think I'm ok. Been to Brazil and other countries where I have my wits about me and my wallet and cellphone close to me
3.Staying near Barrio Italia
I'll assume you want a more Chilean experience, wealthier side of Santiago is quite bland, they like to pretend the live in the USA.
Check barrio italia for sure, bellavista, brazil and lastarria are nice too, just don't go in the evenings to avoid the protests. Things have picked up so I'd recommend not going after lunch time.
Never have more than two terremotos.
Galindo is in Bellavista and has typical chilean food. There are other nice places in Patio Bellavista and constitucion, just avoid coming here in the evening
There's a growing local beer scene, you can checkout Bar Spoh, Pepperland, Apiádate de mi, on tap, intrinsical if you wanna check it out.
If you wanna check the current situation go to plaza italia and GAM in the morning. If you still have time, check out cerro santa lucia. I'm currently out of the country but live in this area, it was fine before although unsure how things are now. Check
http://www.galeriacima.cl for a live video stream of Plaza Italia.
Go visit Cerro San Cristobal, if you enter close to Bellavista you can take the Funicular up (cable car) and then take the teleferico on the way down. There are also many trails if you prefer to walk. Make sure to have a mote con huesillos at the top.
If you take the teleférico down you can go checkout sky costanera if that's your thing.
Let me know if you have any questions.