My dad is a contractor and he works on properties in Boston and sometimes he shares with me the prices of these homes and condos and it's SO MUCH.

Is a new garage w/ apartment (and running plumbing, sewer, electric, etc) going to cost me a lot more than 100k?

Draws would go directly to contractors once their info is received.

The electricity is good during the day.

Seeking recommendations on masons or foundation contractors in Western Massachusetts

Hopefully this will clear things up:You are correct with your understanding that you can't write off any costs related to inventory (the house) - whether that be the cost of the house, or items to improve the inventory (like lumber, paint, contractors, other flipping expenses).However, if the cost does not relate to the purchase or improvement of inventory (the house), it can be written off as operating costs, as you noted.

I have been a Carpentry/ General contractor for 15 years now. 

The contractor that I am hiring to do the rehab is going to be at the Duplex.

Can anyone recommend a good contractor on the west side of Cleveland?

There are lots of reasons why the person isn't getting a loan even though they have that much cash: could be maxed on the number of loans (10 usually). credit issues, contractor (1099) employment, etc  It can sometimes help if the buyer can provide a credit report to make the seller feel more comfortable.Good luck and welcome to BP!