Right now I am in the process of learning as much as a I can and saving until I can semi-comfortably invest in my first property.

Using your existing portfolio of real estate as collateral, you can get a revolving line of credit, a long-term amortizing loan, a short-term amortizing loan, a short-term semi-amortizing loan, etc. 

I have business line of credit , but the interest rate is too high to think in any passive (or semi passive ) investment that I can use that funds for. 

Alas, is there any regular or semi-regular meet up in the area?

I'd say, if you were going to do that part of things, maybe you should flip locally (or semi-locally).

By scaling this, you would be able to create strong semi-passive income which will allow two things: more money to invest in something else, such as buying rentals, as well as increasing your income if you wanted to take out a larger residential loan from the bank.

I also overpaid a terrible contractor to remodel a unit and then had to pay one semi decent contractor and a good contractor to finish the job (I also did some of the work).

However, it is very difficult to house hack with small living space and a live-in girlfriend with a large, semi destructive dog (I wouldn't change the dog part though :)…) Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

It appears that taxes are paid semi-annually in IN, so what's the reason it's all on you?

Connect with some local or semi local developers and get some proposals.