I know in Boston there are courses where you can get through the classroom hours in a couple of weekends. 

Look for places close to transportation like train and subway stations and close to a commercial corridor. 

My wife and I are in the process of moving back to the Philadelphia area (currently in Boston) in the fall and are actively looking at owner occupied 2-4 unit opportunities in the Philly area.  

I'm from the Boston area, i'm guessing location makes a difference when getting qualified.

So I've lived in the same apartment complex for the last three years, just north of Boston.

Austin, Boston,Tampa, Raleigh , Denver , Seattle etc.Boomtowns for the young and smart.You are in a very enviable position to have the option to go to where both the great Real Estate deals and the 25 year old woman are hot and available.Some of the most popular cities for the young and educated have historically bad rent to value ratios.

You were right, the house is located in worcester on a main road with public transportation.

Its fairly easy to estimate hard costs like materials and labor, but what often gets overlooked is soft/holding costs like utilities, insurance, taxes, permits, grass cutting, costs of funding, transportation, survey, selling costs, commissions, advertising, time delays and contingencies.Make sure your numbers are strong.

In most towns in the Boston area the numbers simply aren't amendable to a buy/hold landloard strategy.

They sure aren't in Boston, or probably an hours drive of it.