Then there are the challenges with Section 8 tenants paying utilities and taking care of their rental property.

For example, I have a subject property that has 1682 SF on the main floor and 810 SF of finished basement (the majority of which is about 8 feet in height with the exception of some bulkheads to hide the mechanicals) and 271 of semi-finished basement that is a utility room basically (washer/dryer, freezer, hot water heater, furnace, some storage).

As well as utilizing them to market and sell your properties.

My wife not comfortable putting our house as equity, therefore we are utilizing other options to fund investment properties. 

Purchase price: $302,500 Cash invested: $5,000 Utilized VA Loan for a House Hack for my first Rental Property.

We are not real estate professionals.1) How would you handle the classification of the property in the 2023 tax year and would you utilize a STR depreciation strategy?

- Usually a 5 unit with a boiler means that all the units share the boiler heating system.Which specific utilities in which units are paid by tenants vs shared?

The income includes things like late fees, a rented garage, and utilities that are billed back to the tenant. 

I'd be surprised if the complex doesn't have individually metered units so you may be able to eliminate the utility expenses unless those are for common areas like walk ways, parking lot or laundry.

I'm assuming you are arriving at your cash flow number by applying Gross income - cap ex, maintenance, utilities, vacancy, tax, insurance, mgt, landscape/snow & Debt service?