If your searches are basically copies of the chain of title and you don't provide  your clients with a cover sheet (in our area all the searchers do), then I'd suggest investing into a good software program like DocuDesk or full install Adobe.

You could can in your docs, turn them into Word format and cut and paste everything into their website as requested.

You could add a disclaimer that you are not responsible for possible errors in the software conversion process and that only the original copies pulled from the county are considered the "actual search".

Add that they are responsible for reading/examining the county copy search, they responsible for any typographical errors and proof reading whatever you upload into their files and that you are providing a search only and by cutting and pasting the information into their system, does not constitute examing or reading the file. 

Basically, they are asking YOU to be their title examiner.  Since it would be the examiner/reader who would be typing all this into their software system to create a commitment/binder.

I'd just say look, I can scan into your system either via PDF or Word.  But if we do the Word conversion on our side, we will not take responsibility for an errors in conversion. (NOTE:  Word/RTF is NOT backwards compatable, so if you have a higher version than they do or visa versa, it will not read earlier version at 100% conversion rate)

Just a thought.  Personally, I'd offer to scan it in as a PDF "locked" file so whatever they get is EXACTLY what was pulled from the county.  Let THEM do the conversion and hey, you can even suggest the software programs mentioned (and there are many more starting around $50 for 1 user)

Best of luck

p.s. As a Senior Examiner, reading for several different companies on several different title software programs, I would NEVER want someone else typing in info into my files since I ultimately, am responsible for any errors.  It's an unnecessary duplication of effort and to me, a real time waster.