The recruit gear will work for the easier HM's and story OP's, quicker you get it upgraded the better though. As for getting more orange gear, 2 easiest ways are GTN or legacy vendors on Coruscant, will take some serious time and money to kit out a full set of orange gear with mods though.

Except unless i'm blind (quite possible) you can't actually whisper someone from the guild window

Some of the visor headpeices do hide the hoods, but only if the head slot is visible. Hide your helm in options and your hood comes back. Stupid thing is that it just proves the hooded gear models are capable of having the hoods removed on the fly

The fact that almost every Jedi NPC on Tython has hood's down is just rubbing salt in the wound. Pretty obvious from those NPC's that the models with hood's down do exist so chop chop Bioware and give us the option.