I have the supply (borrowers) but I’m looking to raise money to fund those mortgages.

PMs are regulated in NC.

What your CPA has recommended is you receiving rent "income" in the form of a personal service barter, so you would still technically have to report the value of the chef services as rental income.Now it's true, most people don't report barter services, but in this case there is a vast difference between what the tax regulation states vs what people actually do.For example, as a CPA, if I do your tax return in return for mowing the lawn at my house, I would still have to value the amount of your lawnmowing and declare that as income. 

You have teams that are new to the game, and while they may charge less, you want to make sure they are up to date with compliance regulations and are staffed to adequately care for their tenants.

I think it boils down to supply / demand for housing but, nevertheless, I'm sure there is a lower limit on what return investors will accept.

First, contact your zoning/permit office and find out their guidelines/regulations about pools and the enclosures needed. 

The areas you talked about - Quincy and Boston would have better inventory for 3-4 units but towns like Arlington would have some supply of multi (2 families typically) and Lexington is virtually none.

Of course location, supply and demand all come into play as well.  

Be mindful of regulations and specialty taxes imposed on parking operators. 

With the water supply lines underneath the home, it's important to wrap them in heat tape and make sure the skirting is always secure.