In most states as a sales agent you will have to work for an agent and they will have requirements and sales expectations. 

Based on the listing price of the second parcel, my friend expects it may take 2-3 years to sell.

I expect them to return less than I can do personally but it's worth it to me to free up my time.But I doubt I will ever stop directly investing in Real Estate because I just enjoy it and like to stay busy.So, you can see, it's kind of a personal decision.

Door was broken. 

Also to further refine what i meant by Boston, I am foucsed on investing in South Boston, East Boston, Everett, Revere and Dorchester as I expect the greatest growth there.  

As a purpose built rental the price is generally driven by the rental income not the emotions of buyers.Pull your home equity to invest but do not expect to be reliant on the income when you are unemployed in 4 years.

However, that is always made exceedingly clear before the deal begins so there are no misunderstandings.So without knowing what was said, implied, or expected with your friend.

For instance, I never expected my basement to be cleaned of cobwebs or dirt on the floor, but City Waterproofing power washed my basement for me.

I was planning on purchasing a 400k MF with cash but was planning on getting a line of credit on the piece in order to handle any "expected" surprises. 

I think having realistic expectations about beginning is helpful.