Hm, I'm not waiting to get my time investment back or something like that xD I just genuinely, got like messages for example this person messaged me on facebook and said "Hi, how are you?" and I replied to them and the conversation basically died there cause they replied with one word answers. Even though the conversation never got anywhere, they repeated this over and over, so it was a bit pointless
But yes, like, this person was the one initiating the conversation, I didn't expect anything XD I just find it weird and awkward.
I'm capable of following conversations but not when the other person replies with one word answers lol
But yes, since I know it's a struggle to make conversation I try to be more creative with my replies, since I know first hand how impossible it is to reply to one word replies lol
I actually don't really understand what you mean with wanting to get a return on investment with the conversations since well, uh... I adapt to the person I'm talking to (?) I have chatty friends and quieter friends, I also have friends that prefer to listen instead of talking so you just adjust (?) Kinda just accept people for how they are kind of thing.
But on the internet, when you try to engage and everyone ignores you (like on a server on discord) well, how can someone not feel awkward in that situation lol, or like this person that initiated conversations just to not reply more that one words and then not reply at all, haha.
And I dunno, you can put effort in the conversation but a conversation involves two people, so... I'd actually think your words apply to the person I'm referring to lol. I'm well aware I'm a chatty person, it just depends on whether the other party wants to make an effort themselves XD
As for people thinking you're a negative person for disagreeing, well, that's really childish I mean, people won't always agree on things and it's totally fine to disagree, it's called having an opinion and I really respect those who do so in a respectful manner while keeping a firm stance on their thoughts 
Sorry if my reply is weird, I didn't really understand what you were trying to say. Was it like to me or was it like speaking of people in general?