We were swapping horror stories.My understanding is that even asking the question is presumptive evidence of discrimination.Again, this is in the People's Republic of Massachusetts, where all landlord's are considered to be greedy, rotten capitalist, slumlords who make their living from the sweat on the backs of the working class.Substitute a different protected class though and see how the question sounds.Someone calls the landlord about a rental. 

Keep it as is, don't be greedy on this.

It's better to not be greedy on the first one or so until you are comfortable in the business. 

When others are fearful be greedy I believe is the saying.

The Financial advisors you are referring to as having been educated all get paid commissions, the day traders get bonuses based on how much money they are able to bring into their perspective firms every year, they make somewhere between 1-2% of a clients total book and they get paid for every trade that they make "for their client"  for the life time that the client remains with them. 

(if he calls back raise the your "asking" price by $10k each call).That SHOULD get you on his  "greedy whacko nut job" list.

Be greedy when others are fearful and fearful when others are greedy" - I'm not seeing a whole lot of greed out there right now.

It is about the DEAL, it is about the property, NOT the end buyer, their mood, their greediness or what ever else.It is the wholesaler that NEEDS to know what profits that house would have as a flip, or what the numbers would look like as a rental etc. etc.Please understand that this is not an opinion.

One thing that I see, is that a lot of GC's are greedy, and don't respect long term clients.

Would it be greedy of me ask for a 5 cap on a 100+ year old 2 family building?