And congrats on taking the first step by joining the conversation.

Always get your conversation about how you get compensated out of the way FIRST!

With the statement from the kid in hand, the investigator confronted the thief, they had a long come to Jesus conversation.  

I suggest reading "Crucial Conversations: Tools for Talking When Stakes Are High" by Kerry Patterson  and "Guerilla Marketing" by Jay Conrad Levinson.

I'm not saying go to monthly REI meetings, I'm saying talk to Realtors, talk to people anywhere you can strike up a conversation about RE.

I'm walking through a for sale by owner income property in the near future - is it appropriate to have a casual conversation with the owner about if they are firm on price or does it really need to be done with a written offer?

I will look into this for Massachusetts at some point but for the sake of carrying on the conversation is anyone from Massachusetts familar with a "Notice to Enter" brief explanation would be nice....

Conversely, recording an amount on the lease, less than the amount collected, is blatantly dishonest, and, in most jurisdictions, certainly illegal.  

Any recommendations on conversations I could have with my property manager on how to proceed?

Well if you want It to be a 4-plex and it is no longer allowed after the re-conversion to an SFR because you lost grandfather rights then you can't use it for what you are buying it for.In that case it doesn't make sense.