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This is a highly specific scenario for which I haven't been able to find a concrete answer.

When you write the contraction 'Tis (It is), should the apostrophe be an opening or closing apostrophe?

A lot of typefaces have a mirroring design for apostrophes where the opening one curls one one way and the closing one curls the other way.

If you just start a sentence in a text, it doesn't seem to matter as long as you are consistent about it, but then you have lines of dialogues.

So if you start a line of dialogue with the contraction 'Tis, you have an apostrophe right after quotation marks: "'Tis the season..."

So there are two scenarios: in a line of dialogue and in a regular sentence. And there are two apostrophes: the opening and closing one.

Which should be used where in these circumstances?

Dudenheim
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Pretty much any software that does “smart” quotes will get this wrong. The correct typesetting for a leading apostrophe is ’tis and not ‘tis (which is what you'll get with smart quotes).

Contrary to what Sciborg has written, there are three apostrophe-like symbols available:

  • ' which has no place in polite company and should only appear in code listings, descriptions of keys on the keyboard and attempts to forge typewritten documents.
  • ’ which, is properly speaking, an apostrophe. This is used for all contractions, whether it appears at the beginning, middle or end of the word: ’tis, ain’t, steppin’. It is also used as a closing quotation mark (on the outer level in most British publications, for quotes within quotes in most American publications).
  • ‘ which is a single opening quotation mark. This is the devil that messes up smart quotation software since when it sees the sequence ' it thinks you must mean the opening quotation mark, even when you don't.

On a Mac, you can directly access the single quotation marks with opt-] and opt-shift-] for ‘ and ’ respectively. Windows expects some bizarre numeric code incantation using the alt key and the number pad. The easiest way to get the correct apostrophe in most software on Windows (or Mac if you're averse to using the opt sequences I mentioned) is to type, e.g., a'Tis and then remove the a.

D. A. Hosek
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So first of all, you are correct that there are multiple types of apostrophes. In some typefaces, and in Unicode/UTF-8, there are two types of apostrophes.

  • The typesetter's apostrophe (’), which is the "curly" one.
  • The typewriter's apostrophe ('), which is the "straight" one.

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To quote Wikipedia's decision on this matter:

According to Unicode, the apostrophe is the same character as the closing single quotation mark, although the semantics of this character are "context-dependent". (When it functions as a closing quotation mark, it is always paired with an opening quotation mark.) Other substitutes such as ´ (acute accent) and ‘ (opening single quotation mark) are common due to ambiguous treatment of the apostrophe in early digital typesetting (as explained below). In informal contexts, the simple typewriter apostrophe ' is commonly substituted for any of a variety of similar marks and their formal purposes.

In informal contexts, the default apostrophe is that flat typewriter's apostrophe. The only situation in which the left-and-right-curling typesetter's apostrophes are used are in opening and closing dialogue. Otherwise, use the flat typewriter's apostrophe.

So, to answer your specific questions:

  • Words like "'Tis" should always use the flat typewriter's apostrophe.
  • When you have "'Tis" in between opening and closing dialogue quotations, you would use the curly left opening apostrophe and the curly right closing apostrophe for the dialogue marks, and the flat typewriter's apostrophe for "'Tis" itself.
Sciborg
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That is up to the typesetter and the font they have.

You on your PC keyboard just use a single apostrophe when you start with a word variation that requires the leading << ' >>.