My DD1 is really clingy exhibiting many of the behaviours you described also, I had wondered if it was because she was weaned at 9months (when I caved to pressure from family etc) and because I had let her cry etc where as DD2 (who is pretty chilled out and self sufficient) was BF until she self weaned and coslept until she needed her own space. So almost the complete opposite scenario - apart for the looking for a reason,lol.
I think a huge proportion is innate personality as well as the influence of environment!
I would certainly look at getting your DS assessed as other have suggested but do keep in mind all kids are different and this may be his personality to a degree. Seeking advice on methods to support him and help him develop a good internal dialogue to assist him will make a massive difference to your confidence (FWIW sounds like you are doing a fab job).
DD has just finished her first term of kinder and it has made a massive difference - I cannot describe how much her behaviour and confidence has improved. I have to remind myself she is still really young too.
I can also second Lulu's recommendation of the Bach remedies - has worked wonders here for everyone, from DH down to the stressed out pooch
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