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As it happens, I was facing the same question as you are now, just last year. I`ve managed to get a good entry level sites and am going to list them below. However, the most fun I had was playing with Kali linux, maybe give that a shot as well. Also, another entry level tool that you can play with(and I highly recommend it) is OWASP Zap - Proxy attack - ...


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Beyond the regular web functionality like login, navigation through the site, launch I would suggest using hardware simulation to fake mouse and keyboard inputs. I think that the easiest solution will be one of the single board computers like Raspberry Pi, see this thread for example



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