However, I am new to flips and am trying to get some feedback.....The house was built in 1915 and is 3235 square feet.

You've got to learn the language of contractors so that you know when to spot red flags.

Our market is sort of an anomaly- my state is extremely red and business friendly, but the city where most of my investments and my clients' investment are is a blue enclave.

When it comes to new construction, there are cost per square foot figures available to your local area from banks, insurance companies or experienced builders.

However, the House behind it sold for 430k and is half of the square foot.

I can provide specific numbers and figures if anyone is interested, but a quick breakdown of figures pending the rental income I believe is a good price (lower than a rental analysis I had done on the property) - we would come out essentially even annually or maybe barely in the red (if we are conservative with savings for improvements, maintenance, emergencies etc). 

The square footage is 1640 sqft.Does anyone have any good roofing companies in that area?

Prices east of Worcester towards Boston have become untouchable for the "common folk," and first time homebuyers in the Metro-Boston area are being pushed as far west as Worcester.We made about 15 offers before we got a bite on a 4 bedroom, 2 bathroom, 1600 sqft home in the Webster Square area of Worcester.

Purchase price: $40,000 Cash invested: $140,000 Sale price: $288,000 Complete gut with 700 square foot addition to rear of property.

Based on the existing layout, I can easily convert it into fourplex with 4 pieces of three-bedroom units, each with area of 1,200 square feet.