@Jordan Deschamps your task will be finding a good house suitable to your objective which is likely to add a suite, add a garage, fix up the part of the house you will live in, then managing the rehab.

Talk to others who have been doing what you want to do already and get some objective points of view along with your own research and make your own decision as to best route you should take.

Tax auctions are great if you buy a large quantity of of properties because then the law of averages will work it all out.3) No idea.. but refer to answer #1. 

Elevate yourself from a construction/flipper guy to the go-to source for meeting his/her financial objectives.

It sounds like you are WANTING to believe this will work and finding reasons to justify that it will rather than look at the situation objectively.

I am looking for my first deal -  a duplex in Brooklyn, New York where I can rent out one of the units for $2,000/month and purchase price is under $750K.The more specific your goal/objective, the easier to reach it.Lastly, be sure to check out the BiggerPockets podcasts, blogs, search function (top right corner), and stay active on these forums to find folks who can add value to you (and vice versa).Best of luck to you moving forward,Abel 

Ultimately I'd avoiding using a chimney for a wire run because it just doesn't seem right and when you go to sell the house if the buyer gets an inspection, and the inspector is good, it will likely come up as an inspection objection issue. 

They brought up possibly paying a larger deposit and spoke with me to try to isolate our objections to see what could be done to change our mind.

That's half the battle when you get into real estate investing in finding out what you like to do and what meets your investment objectives.

The Planner will write an objective staff report detailing the proposal.