Are you sending him a PDF on InDesign file?
My suggestion: send him a PDF, and DO NOT convert fonts to outlines.
There is no need for that if you send a PDF. But, if you are sending an InDesign file,
package your document, and that will also include all used fonts.
If you send fonts to your printed, he needs to have licenses
for those fonts in order to use them legally.
Hope that helps.
There is no good workaround for what you want, you will always loose your font attributes.
CS5 is a lot harder to convert fonts to outline. In CS4 converting all fonts to outline was easy but considered a hack and not recommended.
As bob says if possible find another printer but if not possible try converting the fonts to outline in Acrobat Professional. But what ever way you do it the fonts will not look the same as fonts not converted to outline.
i agree with everyone here.
adobe employee Dov Isaacs answers that question best in this thread:
has the OP asked the printer WHY convert the fonts to outlines? in the age of modern RIPs and software it seems extraordinary that this request is still made.
The request is asked more then you think. It is no where near the best idea but it still happens, and saying to someone, Find another printer. is just a waste of time unless they happen to have another printer handy to go to.
I found a good use for converting to outline today, Digital job came in and they used small thin fonts in a full black reversal, when we printed that job out the text filled in an was hard to read. I converted the fonts to outline and printed it out again and would you believe the text was quite readable.