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. 

It's easier to batch the calls than convince yourself to make one call each day, so dedicate a time slot to get it all done with real conversation rather than becoming just another applicant. 

Their site is here: http://www.meetup.com/Real-Estate-Investors-of-Kil...I've been several times now as a Realtor in the area, and its been a relaxed bunch and good conversation about local real estate and investing.I have a fourplex myself in Killeen - when I was still active duty, I did the same thing, and bought five homes before leaving (two with the VA loan - you can actually use it twice).I wish I had just bought fourplexes - they are more work, but they pay! 

Deciding to be an ACTIVE member on the forums and engaging in conversations is one of the best things you can do to learn and network.