Now I have seen a situation where there was a pre-2016 build, but the previous owner pulled permit to install a pool and a new Certificate of Occupancy was issued after 2016. 

@V.G Jason It is true that a duplex limits your rental pool. 

That area’s known for its classic charm and high-quality homes, and if you handle this right, you’ll be tapping into a buyer pool that values both style and substance.

If one or more units are vacant, the remaining units often don’t provide enough cash flow to cover expenses, making it harder to meet operating costs.Maintenance costs: A fourplex comes with four times the appliances, plumbing, HVAC systems, and other components to maintain, leading to significantly higher repair and maintenance expenses than single-family homes.If you want to see the detailed calculation, read this BP blog - More Units Doesn’t Mean More Money—Why a Single-Family Home Can Beat a Fourplex.Resale value: Multi-family properties have a limited buyer pool—mainly investors—who base their offers on CAP rates.

We have an accountant with a chart of accounts to manage everything but I do not see why you need one for operating expenses vs. income.

Unfortunately - there are a couple of issues here that likely make this hard to finance:-"Cabin style" dwellings typically are difficult to finance as the secondary capital markets treats these differently than standard single family homes as the buyer pool for a "cabin" dwelling is less than that of a standard home.- Yurts: Lenders typically have difficulty financing Yurts as they are moveable collateral.

The buyer pool is beyond flakey..Your best bet is a local investor.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Can anyone provide insight on the average cost of insurance for Airbnbs with pools in the Boston area?

So let's assume you have significant enough equity in a property to pool together a reasonable amount of starting capital.