That should really be the deciding factor...is it necessary and a large enough project to include the permit process?

South End is great for appreciation-driven investors who want to be close to the action.NoDa (North Davidson): The artsy vibe and walkability have made NoDa a magnet for young professionals, driving appreciation in this district.Kannapolis: Known for ongoing revitalization projects, Kannapolis is positioned for appreciation.

CT is 1-2 hour drive from my location depending on the town and is manageable for one project.

At 19, your friends may not understand your drive.

Financing is important but your realtor will absolutely be the determining factor whether you purchase correctly or not. 

These days as you mention with STR almost everything can be handled remotely...cleaning, painting, locksmith, yard care, even drive by pictures of the house occasionally or internal pictures too. 

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

This will help you understand the qualifying requirements, key factors to consider when purchasing, and how to assess whether a property might be a good investment at first glance.

Quote from @Tio Sam: Quote from @Zachary Deal: I agree, I would drive some properties that have sold as flip.

In terms of the areas, you will be best served driving it.