Since I had bought and sold quite a few of my own properties already and was comfortable with the contracts and the process, it wasn't too much of a stretch for me to help others buy properties.

Rachellette McKissack I would pay off your other than school debt bills off just enough to where you're comfortable putting a decent amount into your savings.

Our goal is to be able to do the type of work we care about while still securing a comfortable life for our family and healthy retirement plan.

They will want to see that you have a basic, stable life situation for you and your child- probably meaning a stable job, a stable place to live, and a stable car that gets you to and from.

I'd need a several hundred thousand dollar HELOC to be comfortable drawing on it to finance a downpayment on another property (I'm pretty sure a conventional loan would make more sense, but again I'm not an expert).

I advise you to visit any market and any team you are considering working with to develop a comfort level that will get you over that hurdle.

Must be comfortable with quick cash closings, assignment of contract, double-closing, subject-to and other creative investor strategies.  

Plus, my failure risk right now will be somewhat low as I will be living in the other half of the duplex, and can cover the mortgage comfortably with my full time job (I still recognize I'm taking some risks). 

- I have been told it is easier on sellers to use a standard real estate purchase agreement from office depot as it is not intimidating to sellers and it makes them more comfortable, what are your thoughts?

That involves consideration on forming a legal entity that you might have to hire someone to advise you,  figuring out your financing that you pe-qualify for and get a loan letter from the lender that will help you and give the owner a comfort level, and a new business location that is convenient and has minimal distractions.