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Let's use できる as an example.

できる (I) can do (it)/possible (action/event). できるか? Can do?/Possible? できますか? Can do?/Possible? (polite)

Believe it or not, できますか? still sounds too direct to me.

Now here's my question, is this dekimasuka?:

(もし)できますでしょうか? Possibly can do?/Perhaps possible? and (もし)できませんでしょうか? Can't (you) possibly do?/Isn't it perhaps possible?

If the above statements are grammatically sound, how about natively? When a native person hears it, what is their average response to such a statement/question?

Another related question: according to some teachers of Japanese, the か at the end of a question could be considered harsh, too direct or unnecessary. For example, what is the difference (if any) between [たべる?] (with question mark) and [たべるか?] (with question mark and か)?

Optional question: Where does だろうか? and でありますか?/でありませんか? fit into all of this?

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A plain form + か does sound a little more rough or direct, I think. Normally it would be said without the か or with の instead as it's a little softer. できますか, however, is not direct at all and is a totally acceptable way to ask something politely.

In polite keigo type situations, you may in fact here できますでしょうか or いただけますでしょうか. Technically this is incorrect. You might call it a form of 二重敬語 (maybe, don't quote me on that). However despite it being "wrong," you still might hear it from time to time. Kind of like ら抜き言葉 (食べれる) or omitting the い in ている (~してます). So yeah, it's possible to use it this way, but be aware that doing so is breaking with convention.

The standard way to say it in these situations is, of course, plain form + でしょう, so できるでしょうか and the like.

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As always with downvotes I'd appreciate if someone would tell me if I'm wrong about something – ssb Dec 18 '13 at 6:21
Put simply, ~ますでしょうか is not incorrect. It is, however, a little too polite unless you're using the like of 尊敬語 and 謙譲語. できますでしょうか is 馬鹿丁寧, whereas おできになりますでしょうか is perfectly acceptable. – Nothing at all Nov 23 '15 at 17:18

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