I'll try to list a few possible things he might be thinking/doing in no particular order:
1. Showing off. He could be looking for what others think of his looks and trusts you for your opinion. Maybe he enjoys showing off what he's got with no particular agenda.
2. Afraid of possible rejection. Second guessing yourself happens to the best of us. Could be ok with showing a picture of muscles but avoiding the possibility of being shot down if he sends out anything more than that. Maybe this 'is' his way of flirting and either waiting for a big move from you or he gets more comfortable to try it himself.
As it stands right now. I'd say you are awesome friend to talk and show off to. As for the 'not interested' part, it's not 100% clear but it does point that he is interested. You can try bridging that gap yourself if that's what you'd like.
If you'd like any more insight, feel free to ask for more info.
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He just wants to get complimented. Women do this to men all the time "tell me how pretty I am but leave me alone afterwards" lol.
Based from what im reading he's shy and i guess has a low self eestem. Keep talking to him tho and he'll get used to it
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He might like you to just not ready for that next level
LOL, your "obvious" flirting.
Playing hard to get don't be so easy
Stop flirting.
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