For now I wouldn't worry about delegating STEEM.
I personally would advise against trails for now too, at least wait until you have more Steem Power, and choose your votes (maybe on comments to increase their visibility) for the content/authors you really take a liking to. The aim early on is to gain like-minded followers, but it is tough without the 'proof of stake'.
Perhaps look into ,
,
- These accounts do not care about your proof of stake, and reward content for it's content - not the author.
Sorry about the flags relating to that account - I would take a watching brief on those posts.
Good luck!
RE: Am I stupid?