I am quite shocked that pro booleans has done this to your model, Did you apply it after you had turbo smoothed your mesh?

This is how I would approach this model. Firstly I see no need to booleans at all. You have 3 circles that are then going to be pluged with another mesh, there is no need for this just make your pieces and lay then over the top of the base. As for the date all you need to you is select a few faces and extrude them to achieve that cavity.

I know that most architectural work is done using booleans however there are many other modeling techniques that you may not be familiar with. If you need clarification please let me know and I will record a video to show you what I mean.

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Well..the three smaller plates are meant to be a bit below the big one with a chrome metal ring going round on the side as the picture shows, I'm intending to make this effect more clearly, similar to that of the date, but with metal edges, so I can't put small cylinders on top of the big one, if that's what you mean?

When I'm making booleans, say the numbers for instance, I get this singled out lines that runs from them, this prevents me from doing any more work on the mesh if i intend do convert it to an editable poly again, say I want to chamfer the edges of the volyme i booleaned out, it would produce some really weird results, that's why i checked the box "make quadrilaterals" in the advance options of ProBooleans to get a complete mesh again, and it turns out like this, no turbosmooth.

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i would advise you to avoid boolean and proboolean as they both tend to add not needed geometry, proboolean is rather good for simple extractions, and boolean is no good at all, takes more time to clean the mess it makes than to make the extraction your self manually.
For proboolean,lets say you want to cut a tube into you plane, try using a cut tool to cut a box around the area where your boolean will be, that way you can minimize the errors that proboolean makes.
Also consider using a displace map for some details. There's some free or demo versions of programs that creates displace maps from simple texture, also i thing there's a photoshop plugin for doing that.

From your screen shoot, i can see that your model has huge amount of not needed geometry, probably caused by boolean operations and turbosmooth / meshsmooth, it would be great if you can clean that by removing edges (holding CTRL or ALT i'm not sure, while removing an edge, removes not needed vertecies) Although it would be faster if you remodel it.

As you mentioned those singled lines that run from your boolean, there needs to be only one line connecting the boolean with the model on the same polygon, if you remove that edge all hell's gonna brake loose haha, just kidding, what i want to say is that your edges that are made with a boolean operation needs to be connected with rest of the model, they can't just stand in space with no connection to the rest of the model, actually they can, but the result is not pretty.

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The secret of creativity is knowing how to hide your sources.
-Albert Einstein

You should be able to remove that single edge with the backspace key.

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actually you can't remove it, you can only delete the edge and by doing so you delete the corresponding polygon.

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The secret of creativity is knowing how to hide your sources.
-Albert Einstein

I've tried for a few hours now to make it work in some way, modeling from extruded shapes, making booleans etc but I end up with the same crappy mesh that gives off weird reflections due to one vertex holding maybe 20 edges in very acute angles. So I'm dropping it. It's not what I wanted but I need to progress on this model, I made extruded numbers instead..

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Yes, your're right - it all comes flooding back now. I think in the past I've had some success cutting more edges into the mesh, but this may not always be appropriate. It depends on what sort of shape you're cutting out.

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[Link to www.3dprevis.com]