If it is in a C/D area I would not be comfortable with breaking even.It looks to be between Blue Hills and the research hospital.

Once I get to a point that it is making enough per month that I feel comfortable taking money out of the business that would be when I get to the point that it is worth have a specialist assist me in all deductions, credits, and future items that will help me to transfer from a W2 to working for myself fully.

Because of my savings and lack of expenses, I'm in a very comfortable position to make my first move, but because my income is mid, I'm unable to meet the Debt-to-Income requirements to qualify.

Off market deals usually have nonrefundable deposits and a clunkier process that isn't as suited for out of state people until they have good contacts in the area to evaluate the property (mostly contractors that feel comfortable evaluating projects for you).

This i comfortable with. 

@Grant Shipman, I will say, I have not explicitly seen anyone violate these rules (that I know of), but more commonly there are a lot of people who have comfort operating at the margins.I.e. compliance officers/attorneys that stop at the letter of the law may say: "investment manager X, you can advertise your company all you want.  

That said, if you're comfortable with Shopify for now and not looking to go big right away, it could work.

You have to walk home, and feel comfortable.

This gives much better diversification protection across geographies, asset types, strategies, investment subclasses etc. versus putting all the eggs into one basket.The downside is that it's not for everyone, and a person has to be comfortable with turning over control to someone else.

But I generally don't find that clients need to spend that much money on the process when some simple coaching can make them comfortable in their search.