I've always been a fan of the Brunson Building:

I'm pretty sure they're already sold out though, so that probably doesn't help you in your search.
Ultimately, we decided to skip the Downtown Condo route and instead found our home in the King Lincoln District to be exactly what we were looking for. Off the beaten path enough to be extremely affordable while still being close enough to the urban amenities that we enjoy.
As for your specific criteria, here's my quick rundown:
- Bars/Entertainment/Nightlife - 20 minute walk to Gay Street, 30 minute walk to southern end of Short North, 10 minute walk to Carabar, BlackCreek, Yellow Brick
- Transportation - We're a one-car household, and the offstreet parking here is nice. Our second car is COTA, and we directly adjacent to three routes (and a fourth route 2 blocks away) that take us in and out of Downtown within 5-10 minutes. Biking takes about the same amount of time.
- View - We've got a partial skyline view from our bedroom windows. Planning on adding a balcony sooner or later to take more of it in.
- Amenities - Coffee Shops, Restaurants, Arts Venues, Dry Cleaners, Book Store, Convenience Stores, etc... within a 10 minute walk.
- Lifestyle - Mostly older neighbors on our street, but all very friendly people. The area is a bit more laid back, but certain summer nights with big events (at Lincoln Theater or Jazz in Mayme Moore Park) they can pack the streets with music & energy.
- Convenience - Pretty much already covered above.
- Possible return on investment - We're planning on being here for the mid-to-long term, and we're confident that in 20 years we'll have a pretty decent investment on our hands.
Ultimately, the biggest thing that drew us to this area was the home sizes. It's difficult to find an affordable 3 bedroom 2000 sqft home Downtown. If you're just one guy, you probably don't need all of that room, but if you're a 4-person family (possibly 5-person in a few more years), a 1-bedroom loft isn't going to cut it for most people.
Anyway... just my 2 cents.
I'd *HIGHLY* recommend saving the date on June 12th for the City Hop event:
http://columbuslandmarks.org/events/city-hop/
You can tour available units in over a dozen Downtown condo developments all in one day. Always a lot of fun. ;)