I live in the city and love it, but I barely have any whiskers and it sounds like you're pretty mustaschian. You'll probably see some additional cost creep moving into the city beyond just rent - groceries, restaurants, entertainment, etc are all likely to be more expensive, so factor some cost inflation into your analysis as well. If you do decide to make the move, make sure you research what your commute would be from your desired place in the city. Since you're planning to ride your bike to/from work, consider the elevation along the way. Some of the hills will leave you needing a shower by the time you get to the office (but hey, better exercise!). So you know, buses are really slow during rush hours, so if that's your backup you probably won't save a ton of time versus your current commute (mine is 30-50 minutes on an express bus from the Marina to/from FiDi) unless you go in early (before 7) and leave late (after 6). Good luck!