I have thousands of hours experience with Dragon Naturally Speaking, but none with Windows voice recognition.
My suggestions would be:
For 743, have you tried:
"numeral 7 4 3" or "numeral 7 numeral 4 numeral 3"???
For "July 12, 1939", have you tried "July numeral 1 numeral 2 comma numeral 1 numeral 9 numeral 3 numeral 9"?
VR programs usually have more than one way to express numbers and which works best can depend on context.
I'm guessing there is little help in Windows Help? I'm wondering if any books have been written on Windows VR?
Dragon works quite well with a little experience. I could dictate and proofread/manually correct a 5000 word article in about 60% of the time it would take to manually type and proofread/correct the same article. You have to enunciate well and speak in an even cadence. Errors are inevitable and you have to accept maybe 10 or 20 per typical printed page, but often you can go for 30 or 40 words with no errors--when speaking at near conversational speed.
What do you mean by a 4 digit date? Dragon has a setting for understanding dates as naturally spoken and it works pretty well.