Any tips on how I can work my way into the industry as an employee at an entry level and basic position? 

I know some of them don’t need that.I'm in the same position where I know I will need to raise funds for my next rental and a flip seems like the way to go.

I am in full agreement that a positive cash flow is a very important goal, due to the fact it insulates you from gambling on appreciation, equity, and rent increases. 

. $1000 positive cash flow per month seems high.The fact that the property is 100 years old may have a definite effect on your cash flow.

A great introduction that provides actionable steps to get started is Michael Blank’s book “Financial Freedom with Real Estate Investing.”

Before taking action on the property?

Scott's The Book on Flipping Houses, the positively portrayed in that book and in the you tube videos is what drew me to BP. 

So you will be in better position if you buy it little less than $70,000.

I would say if cashflow is positive and your criteria has been met I wouldn't worry too much about the appraisal.

Sounds like you're doing all the right things to position yourself for your first purchase.I couldn't agree more with @David Cruice - I think it will be important for you to find a local bank / credit union to build a relationship.