Without knowing more detail, it is difficult to say whether or not you could recover for all the things you list. However, small claims court tends to be much less formal than District and Superior Court. You are better safe than sorry to ask for everything in court. Be sure to have documentation for each item of damage you are requesting, with specific arguments outlined and ready to support each item of damages. You should be able to add items to your prior claim so long as it does not exceed the claim threshold. You should review the court rules and be sure to provide notice to your ex-roommate where required under the court rules.
Check with your court to see if it is too late to amend your complaint. Get as much documentation as possible and witnesses, if possible. You can claim the losses, but whether or not the judge will award them to you is another question. Good luck.