More randomness below
Note the italics is rambling...

Miri

Caitlin - The fact that Dakota is not a pureblood is probably public knowledge, though beyond the fact that he is a half blood probably little other specifics into the purity of his family is known.  Father's side though is a medium well known pureblood family.  Mother is a half blood Hufflepuff graduate who used to play quidditch and now works for the ministry.  If you look hard enough you can find proof of her quidditch days which ended with Dakota's birth (well a few months before actually).  So Caitlin probably has some purebloods are of the same cloth with Dakota.  Though it may be slightly less than others as Dakota avoids the subject of the purity of his family line in general.  Which also means he avoids being around when the subject is brought up about others.  Other than that I think this is another toss in thread and figure it out then possibly - or maybe I will think of something good later that would make sense.

Teddy - Since they are in the same house, and Dakota's tendency to agree with things probably makes Teddy like having him around.  Even if it isn't obvious Dakota is probably slightly reserved when it comes to Teddy because of his arrogance as arrogance is something that could get him noticed.  Though as long as Teddy is getting himself noticed and not dragging Dakota into it then Dakota will be fine with it.

As for causing and getting into trouble.  Dakota is rather easy to drag along.  Though note his natural tendency is his own self preservation of image, reputation, and self.  Meaning he will definitely attempt to get himself out of trouble if he can do it unnoticed - even if it is at Teddy's expense.  However if getting out of trouble would cause to much notice or effort he probably tries to just accept the punishment instead of arguing.

Jana

Trent - We have a thread and I think that sums up anything I could say here better than I could say it.

Tanai - Dakota is the type that takes the path of least resistance.  So as long as her exaggerations don't draw to much attention to him he would be happy standing next to her while she is doing them.  As if she likes gossip and being involved in things she is probably a wealth of information to overhear.  Plus if the attention is on her it isn't on him.  As for the crying he probably can take that in a stride and would be rather calm about it.  I think there would be a thread by thread basis on his reactions to her exagerations, crying, and spoiling.  Though overall I would say Dakota would have neutral friendly feelings towards her.

Josiah

Dakota is one for observation and someone who is predictable and sticks to a schedule is probably rather relaxing to observe.

Amber - Unpredictable and talks really fast probably are traits that probably make Dakota slightly uneasy - not that he would show that.  However at the same time they mean she is probably paying less attention to his every action which puts him oddly at an advantage in his mind.  He probably takes a notice into trying to figure out what she belives as that is likely the closest thing to continuity one can find with the girl.  As he Dakota is very much the type to attempt to blend into the background so that is expressed in him staying rather bland looking with something near the current fashions.

Shanley
- Smoking and drinking are things that Dakota would likely try to avoid being associated with.  Also if the brother in Azkaban is well known he may try to avoid being around her in public as he would not want to be noticed and associated with that.  No ideas beyond that at the moment.

It is getting late for me so will have to continue this another time.  As my ideas are running a bit thin.