Thoughts on buying a new bike as a beginner

I will never in my life buy a new car but I'm thinking motorcycles may be a bit different. I'm super picky or at least I'm going to be with this investment.

Would you guys steer a new rider away from buying a new bike? I'm pretty sold on the idea of a Honda Rebel 500 but I'm not sure if making that big of an investment right off the bat is a wise idea. There's just not many used cruisers in my area. Only sports bikes and ancient bikes with tons of miles.