YES to Dental Insurance:
These costs would be classified under "Insurance - Other", found on line 15 of your Schedule "C". You will notice it states "Other than Health" and Dental Insurance Premiums are not (as I am sure you know this) classified as "Health".
No, unfortunately, to out of pocket expenses as the IRS, since these are classified as out of pocket, are not categorized as business expenses. It is somewhat of a fine line, but that is the guidance. I hope that helps. Just in case you wear glasses and don't have vision, try "EyeBuyDirect" - they are terrific and very reasonably priced!!!
