You are opening a very large "Pandora's Box". There are several answers to every question that you have listed.
At one point I was very active in the search for vintage guitars and I was lucky enough to find some really nice ones. Some I bought just to flip and buy something nicer and some I bought to keep.
That was before the days of the internet, it's easier to find stuff now but it costs more. Since the prices have increased, the motivation for fraud has increased also.
If you don't know exactly what you are looking for and exactly what you are looking at you have a very high chance of wasting your money.
The epiphany for me came from a 1952 telecaster that I owned. I knew that some things had been changed on that instrument. I had the guitar appraised by 3 of the most respected Vintage guitar dealers in the country. I got 3 very different opinions on the originality of the guitar and 3 very different assessments of the value of the guitar. If the experts can't agree what something is worth then why would you put your money in that market?
Not trying to discourage you but there are a lot of guitars being built right now that compare very favorably with the best of the vintage guitars from any period, and there are almost always great deals to be had in the classified section of this forum.
However if you insist in the Vintage quest there are dozens of books on the topic and once the world reopens that are plenty of vintage shops you should visit.
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