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I think you would get the most information by trying it. There are too many variables, in my opinion, to be confident in deciding what will work.
Having said that, AM in general is very susceptible to interference and weak signal problems. Getting high quality isn't just a challenge; it's nearly impossible.
The cheapest and most fun approach would be to build something rather than throw money at the challenge. Just make sure you don't exceed FCC limits of power. A crystal oscillator, buffer, and modulator would be a kick to cobble up. But you need more than a smattering of electronics knowledge.
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