The short answer is, the bake will work, and it will probably look SOMETHING like what you want (in fact a somewhat common normal mapping trick is to “float” some details off of the mesh, and let the bake project them onto the mesh; the differing bounds won’t cause it all to collapse in on itself like a neutron star and fail spectacularly or anything).
The long answer: Baking (normal maps and AO maps, I assume) encodes information about the angle at which light hits the surface, but NOT profile or parallax.
What this means, in practice, is that you can bake the details to your cylindrical column, but it will only look correct at the piece of the column directly facing you. The sides of the column will appear to be a flat cylinder and all the details will start to look crappy at such an extreme angle.
Ever see those people who paint those crazy 3D scenes on sidewalks? Baking maps is like that. At the correct angle, it looks amazing, but at the wrong angle it looks preposterous.
Normal mapping is really best for details that sink rather than pop; consider the cracks and bumps in a brick wall or wooden door. These details don’t affect the overall geometric profile of the object and don’t suggest detail that we’ll see much of anyway at a side-on glance.
So for your column example, I would look at things like making the low poly have less-smooth indentions cut into the column, really simple shapes for the buttress elements (or whatever you call them, I don’t know column terms), and use the normal map to add detail and smoothness to those. Think of your low-poly as being the raw “cut” of column and the normal maps as being the “etching” of bas-relief-type stuff into the surface.
Save the pure flat cylinder model alternative for a lower LOD, don’t rely on the bake to transform a simple cylinder into a complex asset.