Curious as to how you got VS2017 setup with debugging, I was only successful at that with Atrollic Studio. If you could share some tips that would be great. Remember even the CLR of TinyCLR is made from C++ so you always have to do some work in that code. Just better to have the high-level language support for the main app stuff.
VisualGDB is well worth the price but as Justin says, it just doesn’t compare to using C# and NETMF/TinyCLR
I am trying to debug and work on an ESP32 project just now and it’s hard work with the dev environment using VisualGDB and a JTAG connection. It’s just not as stable or as enjoyable as using USB with NETMF/TinyCLR.