I'll just say up front, there are a lot of the questions you've asked that have no black & white answers. 

Its not so black and white.

Not to say you don't sometimes need some black and white facts, but you'll do much better in your pitch if you know your subject and can relate your position on a personal basis.

In your area, I recommend South Shore REIA, and of course my own Black Diamond group, link in my signature, is a free meeting of 100+ investors every month.

I'm in west Joliet, around Black Rd and Rt 59.

My question is, there is a 40 foot easement going through the property on the south side, Diagram here http://screencast.com/t/x87Oi4ZO Does the house need to sit 40 feet from the black property line?

I run a large group called Black Diamond which alternates between Waltham and Worcester, our last meeting had 106 attendees. 

His advice is to make an investment and get your cash outlay back ASAP and then continue on to the next investment.My initial thinking was to refinance every x number of years while still maintaining an acceptable mortgage that kept me in the black.

They certainly make it known when they want to sell us a mortgage, credit card or investment plan; Why not a big ticket item that could get them back in the black?

I host a group in Waltham and Worcester with a high percentage of seasoned investors, which is meeting next Tuesday, you are most welcome to attend:  https://www.biggerpockets.com/forums/521/topics/320373-black-diamond-worcester-ma-6-21-from-frenzy-to-formality