condo or a duplex in Wicker Park Chicago

The more I think about it.... the more I come across a question of the ages...
Should you buy a condo for around 300K or invest an extra 50-75k and get a duplex in the area that i want...
from what i noticed, when you think about living in a city , a more urban and up and coming area of Chicago.. Wicker Park or Buck town for instance... you have to realize that 300-400k is going to get you nothing more then a modern unit on a single floor or a duplex....
realizing that... I think it is so much better to have a double floor unit rather then a single...
upper area can be designated for comfort and work stations such as library, office/den, study area or a playroom... then the lower or first ,however, you want to call it, can be sharper and to invite and entertain guests....... i guess that's the whole idea of a single family house....right?
well... i guess that our ultimate goal in life is to have and own a peace of land which we call our "home"
now...... when i look at single family homes in this area... the steady trend of prices for a good shape,size and update is somewhere between 550-950k...... which sounds like a lot for someone who is in a medium range bracket...... I suppose....
So...... my question ultimately is? ........
-"can a duplex make our investment feel more like a urban home over just a simple condo? or it really does not matter what the space is as lon

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