I'm looking to test some Morphological Analysis tools, which split sentences
into tokens and provide part of speech and pronunciation information
(specifically, providing kana when given kanji).

I'm after some sentences which automated tools would have trouble with.
Examples of what I'm after are sentences which are difficult to determine the
word boundaries, pronunciation or part of speech. Preferably, examples would
be a more correct interpretation, and be something that could be seen in
actual use.

The best I have found so far is "私はあくまで執事ですから". In a similar vain, is
"にわにはにわとりがいる (庭には二羽鶏が居る)" which only applies to spoken use. An english example
might be something like ["Buffalo buffalo Buffalo buffalo buffalo buffalo
Buffalo
buffalo"](http://en.wikipedia.org/wiki/Buffalo_buffalo_Buffalo_buffalo_buffalo_buffalo_Buffalo_buffalo.),
which is difficult to determine the part of speech each word is.
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grammar syntax ambiguity
Examples of ambigious sentences
I've found several webpages online which talk about the sentence `黒い髪のきれいな女の子`
as a famous example of an ambiguous sentence. (For example, [this blog
post](http://blog.query1000.com/archives/17503948.html)).

Here are a couple ways in which this sentence could be considered ambiguous:

  * 女の子 could mean _a female child_ or _a woman's child_.
  * 黒い could modifies 髪, meaning _black hair_ , or it could modify （髪のきれいな）女, meaning _black woman with beautiful hair_ , or it could modify （髪のきれいな女の）子, meaning _black child (of the woman with beautiful hair)_.

Some of the ambiguities, I think, come from reading the sentence in unusual
ways.
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_I'm looking to test some Morphological Analysis tools, which split sentences
into tokens and provide part of speech and **pronunciation information**._

One of the beauties of Japanese is that there is no need for "pronunciation
information". No diphthongs, "silent e", etc. Knowing the 振り仮名 is enough.

Anyway, not sure of your purpose, but how about this old classic:  
「貴社の記者が汽車で帰社した。」

_another test_  
This will tokenize easily, but there is zero chance it will resolve 「触れない」 to
the correct kana.  
「君はチビだから、あそこに触れないでしょう。」

「触れない」-->「さわれない」-->「さわる」-->「触る」  
「触れない」-->「ふれない」」 -->「ふれる」 -->「触れる」
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1. ここではきものを脱いでください  
a. ここで[履物]{はきもの}を脱いでください。(here, please put off your shoes)  
b. ここでは[着物]{きもの}を脱いでください。( put off your clothes here )

2. このはしを渡ってはいけません  
a. don't walk through this bridge.  
b. keep center when walking through this.
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I think that you are looking for written expressions in Japanese which are
ambiguous at some level.

Of course, an easy way to get ambiguity in written text is by using
homographs, which is often resolved by considering the meanings:

> 書の[大家]{たいか} authority of caligraphy  
>  アパートの[大家]{おおや} the owner of apartment
>
> 彼女は京都に[行]{い}った。 She went to Kyoto.  
>  彼女は消防設備の点検作業を[行]{おこな}った。 She performed the inspection of fire protection
> equipments.

([行]{おこな}った is often written as 行なった exactly to avoid this ambiguity.)

In Japanese, the word boundaries and the parts of speech are often clear from
the form of the words when a sentence is written with kanji. Therefore it is
difficult to get ambiguity in word boundaries and parts of speech. Here is a
somewhat close example I managed to make up:

> この件に関して彼は立場上手を出すことができない。

It is incorrect to parse 立場上手 as a compound word consisting of 立場 (たちば) and 上手
(the common spelling of homographs うわて, かみて, and じょうず). The correct way to
parse 立場上手 is an adverb 立場上 (which is made by adding suffix -上 to noun 立場)
which modifies the rest of the sentence, and a noun 手:

> この件に関して彼は[立場上]{たちばじょう}[手]{て}を出すことができない。 He is not in a position to do
> anything about this matter.
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