Just as important as the Act itself is learning how the Residential Tenancies Tribunal (RTT) {formerly the Office of the Rentalsman} applies the law and the regulations which accompany the law.  

@JD MartinTrash can depend on neighborhood most of these resort home community’s have valet trash service so I have a bench up front but it’s a trash can that guest put the trash in and they automatically remove it.As far as consumables I only provide starter set of tp soap etc. after that they are own their own to buy supplies I specifically mention that in the check in info.

What about compliance with city regulations?

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.