If you want to use a HELOC to get an investment property, that's ok, a lot of people do that.

Flipping is not a great option right now if you aren't experienced because regular home buyers are buying a lot of the dumps and overpaying, spinning the market for trash homes up too high to make any money flipping.

Tell us a little bit more about yourself.

He's licensed in GA and TN (maybe more, that's all I've asked about). 

The house sold as a three bedroom at I believe was $18,000 dollars more than it was originally listed for.

I e-mailed the city council people and the response I got was basically "We're not allowing more than 250 STR's in our city so get in line".

(Approach - 2) - He says that if he is asked to pull permits, he is not responsible for any additional work that the inspector may throw (basically more money out of my pocket on the rehab costs).

You can earn honorable discounts and fees overtime by establishing mutually beneficial partnerships with one lender or broker but squeezing them dry for a lot of hard work and not equal pay isn't something I recommend making a strategy

I would say 30k would be a good amount.You could spend alot more or substantial less.You can save some money by buying quality used furniture off Craigslist or FB marketplace. 

Otherwise it works a lot like any other business, it is being sold on EBITDA