However, I have been working directly for a real estate investment group in Boston for almost 4 years where my job is to find and acquire investment properties and to support the operator of a $100 million portfolio.My first piece of advice to you is to be patient.  

I don't want to ask a million questions, but a brief overview would be great.

Should I be intimidated to sell multi-million dollar properties?

Beyond work and real estate, we are also avid social dancers-blues and swing-and our current living situation allows us to host blues parties about once a month, which we love doing.

I would particularly recommend the Black Diamond event in Waltham who is hosted by BP member @Ann Bellamy, the quarterly meeting organized by @Justin Silverio (he got one scheduled for tomorrow so i recommend you reach out to him) or the NEREIA in Chelmsford.

I am guessing a population over 1 million people would be a good start.

Typically the loan amounts are going to be higher (5 million+ range).  

I am not sure about the market you live in, but I have never had to pay for gas for a contractor or evaluation fees in order to get a bid and I have received many bids in the past from a host of different subs. 

I grew up on Long Island where a 3/2 would run you a half million.

We also had them build our website for us and host it with them.