Most buttons aren't going to send another event while they're "waiting" on the first one to be completed, e.g., another button "pushed" while you're waiting on some other "held" button to get a "released," so you'll have a hard time with that. I have seen some people do something similar, but I assume with just a tap/push of one button and modifying the behavior of some other button if it was recent enough (mostly on the Inovelli forums with the config button on their Red and Blue series dimmers and switches). I don't know what they were doing to get that result, but a variable or similar approach that gets set however you want and is used as a conditional in your other actions might be a way.
For the second thing, that is pretty much why I wrote this app: [RELEASE] Dimmer Button Controller (configure Pico to emulate Hue Dimmer or any button device to easily control lights). This was to emulate the behavior of Hue Dimmers at the time. (Since then, their defaults and devices have become a bit weirder, but it's still the same general idea of cycling between scenes.) You again could do something similar with a rule, one that tracks how many times a button has been pushed (or whatever event you care about) with a variable and perhaps resets that counter after a specific time and again uses this variable as conditions in your actions, and you might have to if you want something that isn't geared towards lighting like my app. But there's definitely a reason I did that instead of a rule. 
