I've made use of a CLR to do this, very fast, did pay about $US 300 for the DLL's but that paid for itself many times over. If you're keen on this I can dig around and get you more details. We use it to generate personalised legal contracts, at reasonable volumes. and never had a miss fire from the CLR so far, this process has been going about 5 months now, so seems quite reliable.
we're really just populating a contract that was composed in word and then really just converting/printing that to PDF.
Tell me if you are interested.
For word to pdf convertors , there are plenty of tools available ; or write a C# code to do that , the code is also available on internet.
Well, I think SSRS approach is well and good enough for this work ...or if BI tools are not available then download the report editor tool , it is free and I think does have functionality of exporting reports in pdf's.
Wondering what I would do next , when I am done with this one