Greetings from Indonesia! My name is Hendra, I am a Java and .NET developer with 3 years of experience. For your windows surface app, it is achievable using Universal Windows Platform (UWP). I believe drawing canvas is natively supported and there should be no issue with that. But generating to word or excel document may need third-party libraries, depending on how complex the document should be.
Also, you mention the app should be system-based, and that any drawings should be saved to system. This means there should be a server somewhere, this should be discussed.
I am new here in freelancer, so I may not have reputable statistics to present, but I can assure you that I will not bid unless I am confident that I can finish the job. Thank you for your consideration and good day to you!