Orange/Raspberry Pi and .NET programming possible?

Question

.NET

Greetings, I am far from programming, for me it is nothing more than a hobby. I am only good at VB.NET.
Task: download a small video => transcode => put it on the server (built-in ftp) => send a POST request to be picked up and then deleted.
Since it is unprofitable to keep the PC constantly on, the choice is obvious for me - raspberries or oranges (the second one is certainly preferable for money).
Three questions for the connoisseurs:
1) Will I be able to upload Windows 10 IoT? And run programs there with a dependency on NET Framework 2.0? In the course of quick googling, I did not find a single example, installing wasps. There are no images of Windows at all on the Russian site of oranges. Through the Linux WINE, how will this thing go?
2) I assumed to encode through some kind of third-party program, passing parameters at startup. Really? How much will a conditional 5 minute avi to mp4 be encoded?
3) How would you solve the problem, what tools would you use without spending a lot of effort on learning being at my level?

Answer 1

Will I be able to upload Windows 10 IoT?

difficult question)
But in general it works for 2,3 raspberries - personally verified

In the course of quick googling, I did not find a single example, installing wasps.

Why not take a look at the original source? https://docs.microsoft.com/ru-RU/windows/iot-core/...
There is also a list of supported devices (with an answer about an orange):
https://docs.microsoft.com/en-us/windows /iot-core/...
and step-by-step installation instructions https :
//docs.microsoft.com/en-us/windows/iot-core/...
with .net2.0 will not be very difficult