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This isn't my puzzle (none have been so far), but one I found.

Rebus

Taking the image above, please answer the three questions:

  1. Why is he likely to succeed in life?
  2. How do we know he's reached middle age
  3. What does this indicate about his occupation or interests?

Personally I find the third one a bit of a stretch, but you lot are much more clever than me.

HINT For #3:

Camping isn't an awful clue for part of this one. Take in where he is, and what else XL may mean (keep it simple).

Puzzle courtesy of the Youth's Companion, Sept. 1879

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As for #3:

He aspires to be a writer since he is intent on letters.

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  • $\begingroup$ Wonderful! You got it! You're getting the green check mark and @hexomino is getting a +50 bounty since he got the first two so quickly! $\endgroup$ – JGibbers Nov 6 '18 at 21:59
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Partial answer

  1. Why is he likely to succeed in life?

    He is bound to excel (XL)

  2. How do we know he's reached middle age

    He is over 40 (XL in Roman numerals)

  3. What does this indicate about his occupation or interests?

    He could be an undercover attaché (under cover attached)?
    He is certainly a-gent of some variety.

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  • $\begingroup$ Damn this makes more sense than my answer for number 1. (also your number 2 is a more rebus'y wording than mine) $\endgroup$ – AHKieran Nov 6 '18 at 15:25
  • $\begingroup$ Very good! Frighteningly quick, too. I'll add a hint for the third one later today if no one else gets it! $\endgroup$ – JGibbers Nov 6 '18 at 15:26
  • $\begingroup$ #3 is still off, I added a hint for it. Again, it's a bit of a stretch, but common in terms of rebus's and puns. $\endgroup$ – JGibbers Nov 6 '18 at 20:41
  • $\begingroup$ For 2, I was thinking about better wording: Ur ybbxf bire 40 (rot13) $\endgroup$ – mpasko256 Nov 7 '18 at 8:33
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1 & 3

He's a well-lettered man, intently bound to excel

2

Because he exhibits male pattern baldness and a mustache

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  • $\begingroup$ Welcome to Puzzling.SE! You are so so close, like 80% of the words for #3 and #1 are there, just jumbled around. I'd check out @hexomino 's answer, he's got the right stuff for 1 and 2 $\endgroup$ – JGibbers Nov 6 '18 at 21:32
  • $\begingroup$ This is my favourite answer for #2 :) $\endgroup$ – SpoonMeiser Nov 7 '18 at 18:31
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See @hexomino's answers for 1 and 2.

What does this indicate about his occupation or interests?

XL also means eXtra Large, so he is a bigger fella that is into large portions of food and requires XL clothing?

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    $\begingroup$ #1 and #3 are wrong, but #2 is really close! $\endgroup$ – JGibbers Nov 6 '18 at 15:27
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Taking what hexomino said for #2, #3 would be:

He is ring leader of a circus (Big-Top/Big-Tent)

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Wild stab at 3:

Maybe he's a political figure of some sort as he's a finely dressed campaigner with extra large in-tent. Wordplay might be a bit of a stretch?

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  • $\begingroup$ Not quite, no real extrapolation is required. Might be a good bounty puzzle idea, though. To come up with a rebus with multiple ambiguous answers, and the best one gets it $\endgroup$ – JGibbers Nov 6 '18 at 21:34
  • $\begingroup$ @JGibbers; or like Punch, where the idea was that the reader came up with a caption that was actually remotely funny (see first picture in article) $\endgroup$ – JMP Nov 6 '18 at 21:54

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