I still have much to learn...I received a Rental Dwelling quote from my current insurance provider just yesterday.

Kevin,You can get a General Liability policy to cover the two parcels as vacant dwellings.  

A lot of South Carolina is really unfriendly to investors of buy and hold properties, so make sure you still cash flow after those taxes.Don't be fooled by the only 2% difference between and owner occupied and non-owner occupied dwelling.

You should be in tune with who will be wanting to live there, and how much they may be willing to pay, as well as what condition of dwelling is customary.  

The difference comes in the rating, the duplex scenario you used, is quoted as a 2 unit Homeowners Policy ( less expensive ) vs. if both are rented out they are now Rental Dwellings which require a strictly Landlord policy.

Who is going to live in the new dwelling is of concern to a bank especially if you are a private person and not a construction or investment company.

I've dwelled on the idea of just going self-employed in a small window tinting business but am worried that would make it difficult when it comes time to sell my house and re-invest in some bigger property especially since I won't have at least 2 years of tax documents for the business.

I am marketing a flip and have often wondered if there is a general opinion on exterior color for a single family dwelling?

I think most podcasts don't focus much on the issues, because it's not something successful people dwell upon.

Perhaps purchase a property with an additional dwelling unit.