Brian
Olde City is great. My best friend used to live there. You arent in Old City which is south of Vine/Ben Franklin Bridge. You are adjacent to Fishtown. It maybe a trendy area for young low budget people but never will be a truly desireable area because of what surrounds it.
I used to work a couple blocks away from Rittenhouse (16th and Walnut) and know it well. Know people on Delancy Place as well. Lots of my friends parents and neighbors moved back to the city after their kids grew up. Mostly in and around Society Hill. I lived in Philly for 30 years and know that place like the back of my hand. I get back occassionally and while my views arent up to the minute I know what its like there.