All three approaches you outlined are viable but web service is easiest to 
set up. 

>From what you described, it seems it would be a low-performance use for 
Racket and only simple data structures will be passed back and forth on an 
infrequent basis. Web service would be a good fit for that.

Out of the last two approaches, the COM approach seems to me to be the 
better one. Although I have never used it, Racket provides MzCOM and .NET 
comes with additional support for interacting with COM from within the .NET 
environment. It would allow you to tightly integrate Racket into your 
application, pass complex data back and forth and achieve higher 
performance throughout, but likely it would be more work. I've used COM in 
the past for C++ applications; in those projects it was always a lot of 
work to configure and integrate COM.

I would try setting up a web service first and if it's not adequate for 
whatever reason (performance, business requirements, etc) then I would try 
the COM approach.

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