During inspection noticed cracks in the driveways and after further investigating found roots causing the cracks and were going into foundation..My main concern was roots damaging pipes before having that issue I had tree removed.Honestly I have no idea how big are Cherry Trees and how are the roots.

The comps concern me as you are probably buying at or a bit above market value, but $400 / mo cashflow for a triplex is nice in this market and is hard to come by. 

@Brandon Sturgill Concerning the the Virginia state regulations I believe to be a licensed broker you have to work as an agent for 3 years, but I am unsure if the degree in Real Estate would negate that.

Many of us who live in expensive markets are constantly trying to allocate capital in RE, but struggle to find cash flowing deals.You might even have the income to pay off a good chunk of a mortgage, but you won't want to refi with raising interest rates, so does it make sense to purchase new investment properties with a "portfolio" of methods?

That method has given me much better success. 

VA Guarantees loans for veterans.Provides guarantee to the lenders for the loan.PMI insurance is not required.The max entitlement is $104,250 * 4 = $417kInterest rates are negotiated with lenderPrepayments penalties are prohibited by law.VA loans can be assumedRequired that the veteran live in the property2% VA funding fee.I am looking at methods of financing a multifamily rental property. 

Use the IRV method Income _ net income void of property taxes and insurancedivided by cap rate say its an A property use 7% = valueI / R =V

We are relatively young I think (31) and honestly at this point in my life I wouldn’t be concerned at placing a monetary value on our time working on a property.

Is that not the normal method, or is it just a Boston thing? 

You will at some point be forced to at the least snake it which can be challenging sometimes or at worst replace it.If it is a flip I wouldn't be as concerned and just replace from risers up or whatever currently needs to be done.