Technically, under this scenario, the vent does not appear to constitute a "structural" change, it may also not constitute a change to the exterior (it depends on what the HOA guidelines say), most of the time an exterior change has to do with adding/deleting doors, windows, and changing the  facade and color.   

Here is a breakdown: full kitchen remodel, new heater/AC unit/ducting, all the sheetrock in the ceiling was replaced (bad roof had caused leaking, so it was easier to replace it all),  new lightng throughout (can-styled LED lights), ceiling fans, and some other electrical work, painted interior/exterior, and tuck/pointing to a few areas of the brick facade.

You are right - the front of that house is horrible - but the big problem is that the mini-roof breaks the facade, and the facade blends with the mini roof.

And yes there will be more maintenance if you have some type of wood siding as a building facade or wood windows etc.

For that all you have to maintain is the outside look, and or take paint/stone facade off the front of the building.  

Most people with any experience will see through your facade if you try to portray yourself as experienced when you are not.You are more likely to get taken advantage of then because you will not be able to ask appropriate questions without blowing your cover.

There was nothing left but studs and the brick façade.

You may need an architect if you modify the facades (like windows positions or numbers), the interior layout (like touching load bearing walls) or foundations2.

I'm just not sure what to install and/change about layout or design features (like spindles on a railing, or the front facade of the house, etc.) to make them look more updated.  

It will broaden the first story of the house making it seem larger and it will break up the tall facade.