We recently switched out from a newish semi-detached infill (ie your typical 3 story narrow box duplex) in a great inner city community to a fully-detached older home slightly further out...for about 5-10% increase in cost, and are pretty satisfied with the move. The infill was a great for us to raise 2 small kids out of, but we had outgrown it the last few years...not necessarily because of size, but more in terms of the layout (it felt like living in a really tall railroad car and we were always on separate floors). There were also some noise/crime issues on our street that were starting to get a bit out of hand because of us being so close to a main street...it wasn't the primary reason, but it certainly didn't help.
Even though our house is older (1930) I have to say from an "investment" perspective, I'm much more comfortable with having my money be mostly tied to the land, as opposed to the building that sits on it, or silly things like finishings. Our infill was a ticking-time bomb...it looked great at the start, but construction quality was suspect, and I was never fully comfortable with having my biggest asset directly tied to a stranger.
As a family of two kids, things we prioritize: Easy access to schools, parks/activities, safety, having other families around, character, elbow room, good value.
Zero effs given about: Easy access to restaurants, nightlife, culture hotspots. Not that we don't like those things...but we rarely get to take advantage of those things in our day to day life, so they are down the list of priorities and not something we need to pay for. On the off chance we go to a restaurant, it's not a tragedy if we have to drive.
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