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I've seen they/their quite often used here on this forum and every time stumbled over it as it was followed by the verb in its singular form. For a non-native speaker it sounds soooo wrong - we are glad to get at least the basics of grammar right. It took me a very long time to realise how they/their is meant and that this was just another case of political correctness (and, of course, we do have the same problem in German too!).
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Was kann mensch tun? :-)
Even when used to mean the singular, "they" takes the plural form. "Can I bring a friend to the play?" "Sure, if they like Shakespeare." (Not *"If they likes Shakespeare.")
I think that "they" will inevitably become the 3d person singular pronoun we use for persons of indeterminate gender. It has a long history in English, including being used by Shakespeare, and it is already very common in non formal contexts.
Aesthetically, I tend to prefer "he" or "his," since that is the form used in so much good writing, especially from the 19th C. (Jane Austen's use of singular they notwithstanding), but it's on the wrong side of history and is already losing out.
At work, our manual requires "his or her," which is awkward and not the way people normally speak, either. Even though "their" doesn't sound quite right, it has less of a workaround feel to it.
Note: we don't actually need a "genderless" pronoun - our first and second person pronouns (I/we, you/you) don't indicate gender, nor does our 3d person plural pronoun (them). And we already have a 3d person singular genderless pronoun (it). What we need, specifically, is a third person singular pronoun we can use to refer to persons (animals, too?) who have a gender, but whose gender is unknown. (And we need a possessive to go along with it).
Off the top of my head, I can't think of a situation where using "they/them/their" would unavoidably cause ambiguity...but I suppose that might happen in rare cases.
"My roommate and the football team are coming over for dinner." "Oh, I'm looking forward to meeting them." [Meaning the roommate, not the team]. But English is full of ambiguities; this would happen rarely enough that you could specify if necessary.
But of course if we look just a little further ahead in the future, we can recognize what the real usage problem will be.
"Do you still want to bring your friend on the hike?" "Yes" "Well, it might rain, so tell them to bring they're raincoat." :-)