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There was the following sentence in the New York Times (September 24) article, titled “Perry and Romney set clear lines of attack”:

“His (Rick Perry’s) shaky debate performance Thursday night in Florida underscored concerns among establishment Republicans and donors about his electability and his skills as a candidate on a national stage — and the difficulty he has had planting serious doubts about Mr. Romney. He also finished a distant second place in a weekend Florida straw poll."

I was arrested to the line, ‘His shaky debate performance underscored audience’s concerns about --- and the difficulty he has had planting serious doubts” about Mr. Romney.’

Is the expression, “have ＋_ing” like “He has had planting serious doubts” common English usage? Shouldn’t it be either ‘he has (had) planted,’ or “he has (had) been planting.” I’ve barely seen the expression “have (had)” directly followed by a gerund or a verb in progressive form.

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You're misparsing because of the has had. It would mean much the same if you discard the word has. Perry had difficulty [doing sth]. The extra word has just adds a touch of "immediacy" in the sense that although it was in the past when he had the difficulties, he's either still having them, or is currently affected by the fact of having had them in the past. – FumbleFingers Sep 25 '11 at 1:19
＠Fumble Fngers. In that case, don’t you need preposition, “in” before “planting,” i.e. “Perry had difficulty in doing something?” Is “I have difficulty understanding English grammar,” instead of “I have difficulty in understanding English grammar” or “It’s difficult to understand English grammar” all right, in the same token? – Yoichi Oishi Sep 25 '11 at 3:23
You can have difficulty doing [sth] the same as difficulty in doing [sth]. Often/usually we drop the "in" because it adds nothing - it's redundant. Your last “It’s difficult to understand English grammar” means exactly the same except it's in the passive voice (you aren't explicitly admitting to having a problem). – FumbleFingers Sep 25 '11 at 4:14
Can I say "I had difficulty paying the tuition?" – Yoichi Oishi Sep 25 '11 at 6:19
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Absolutely (except the '?' should go outside the quotes because it's not part of what you're asking about, it's to indicate you're asking). You can also say "I have had difficulty paying the tuition", which means much the same but brings the time nearer to the present (as before, either still having difficulties, or only just recently got things sorted out). We'd probably say paying for the tuition, or paying the tuition fees, but that's just nit-picking and your version isn't really incorrect, IMHO. – FumbleFingers Sep 25 '11 at 12:33
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It's correct, if obtuse. Think about it this way: ...(the difficulty he has had) (planting serious doubts). He has had difficulty planting serious doubts, and this is one of the concerns.

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I wouldn't really say it's obtuse to double up has had. A little bit clumsy, perhaps, but we've all had reason to do it. Especially if you disguise the first one as 've and put and in between them. Anyway, some people like lots of hads – FumbleFingers Sep 25 '11 at 4:20
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I had had quite a few hads before this myself. :) – xpda Sep 25 '11 at 4:33
John, while James had had "had", had had "had had". "Had had" had had a better effect on the teacher. – Karl Knechtel Sep 26 '11 at 8:41

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