@Nick JonesWelcome to Bigger Pockets.

I'll happily take a higher rate on that small loan in exchange for less points and more money in my pocket.

@Justin YoungbloodWelcome to Bigger Pockets.

The Bigger Pockets website has some investment calculators that can help with this. 

It's in the agent's interest to get your offer accepted but they are not the ones that will be flipping the bill should  the property have unknown maintenance or repair issue which may mean significant money out of your pocket.

The real estate focused CPAs on Bigger Pockets are all set up to serve clients from anywhere in the country or world.Perhaps you might want a CPA that specializes in real estate rather than one that is physically close to you?  

I could also pay more monthly cash out of pocket as my finances allow it but I'd prefer create cash-flow and put that extra cash into other savings or investments.Any other pros and cons of shorter vs. longer term HELOANs?

@Karen HossWelcome to Bigger Pockets.

My broker is estimating around $1000/month expenses on a 30-year, I would put down 25% and after origination fees and  closing costs I would be looking at $45K out of pocket. 

There are other pockets of opportunity within Boston though, from pockets in Dorchester/Roxbury to areas like Roslindale.