it Hasn't been my experience that there are additional certs sold each year, at least in the two counties I have purchased in.

Consider him to be your next/only tenant when screening.It is a major newbie mistake to only consider the qualifications of a existing tenant when taking in a additional person.

I suggest you get an average for the past year, increase the rent by that amount + 10%, and just add it to the rent so you don't have to think about it.Once exception: I put a cap on how much is "included" with the rent.

I know a kid that bagged groceries and he managed to save $50,000 and buy his first home.

We also ended up selling it as a for sale by owner with both parties which kept an additional $30k plus in our pockets.Lots of people we talk to think that we we're lucky and maybe we were on a few things like selling without an agent but I still think that you can put in more money to get more money out.

I would imagine he is referring to being all in (purchase + repairs) up to 80% of ARV (in addition, maybe he has a lender who will loan up to 80% LTV).

Now I have taken an addition line out on our house and wondering what is best with using this money for purchasing another property? 

If you can recouped your cost within 2 years with the additional rental income then the expense is justified.  

Now that I feel I have decent knowledge base I am excited to start meeting other investors and developing relationships to help take me to the next level.I am 31 years old, married with 2 small kids, and work as a Physical Therapist overseeing a clinic in the west suburbs of Chicago. 

Additionally, the real estate company who sold it to me reached out and said they would be willing to buy it for 620k.